Home / Articles / The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis

The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis

Yuliya Sergeevna Kudyakova 1
Yuliya Sergeevna Kudyakova
, 
Denis Nazarovich Bazhin 1
Denis Nazarovich Bazhin
, 
Marina Valeryevna Goryaeva 1
Marina Valeryevna Goryaeva
, 
Yanina Valer'evna Burgart 1
Yanina Valer'evna Burgart
, 
Viktor Ivanovich Saloutin 1
Viktor Ivanovich Saloutin
1 I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, Ekaterinburg
10.1070/RC2014v083n02ABEH004388
Published 30 November 2013
Communication , Volume 83, Issue 2, 120-142
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Kudyakova Y. S. et al. The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis // Russian Chemical Reviews. 2014. Vol. 83. No. 2. pp. 120-142.
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Kudyakova Y. S., Bazhin D. N., Goryaeva M. V., Burgart Y. V., Saloutin V. I. The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis // Russian Chemical Reviews. 2014. Vol. 83. No. 2. pp. 120-142.
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TY - JOUR
DO - 10.1070/RC2014v083n02ABEH004388
UR - https://rcr.colab.ws/publications/10.1070/RC2014v083n02ABEH004388
TI - The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis
T2 - Russian Chemical Reviews
AU - Kudyakova, Yuliya Sergeevna
AU - Bazhin, Denis Nazarovich
AU - Goryaeva, Marina Valeryevna
AU - Burgart, Yanina Valer'evna
AU - Saloutin, Viktor Ivanovich
PY - 2014
DA - 2013/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 120-142
IS - 2
VL - 83
ER -
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@article{2014_Kudyakova,
author = {Yuliya Sergeevna Kudyakova and Denis Nazarovich Bazhin and Marina Valeryevna Goryaeva and Yanina Valer'evna Burgart and Viktor Ivanovich Saloutin},
title = {The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis},
journal = {Russian Chemical Reviews},
year = {2014},
volume = {83},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2014v083n02ABEH004388},
number = {2},
pages = {120--142},
doi = {10.1070/RC2014v083n02ABEH004388}
}
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Kudyakova, Yuliya Sergeevna, et al. “The use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds in organic synthesis.” Russian Chemical Reviews, vol. 83, no. 2, Nov. 2014, pp. 120-142. https://rcr.colab.ws/publications/10.1070/RC2014v083n02ABEH004388.
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Abstract

The review focuses on the methods of synthesis of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds and their chemical transformations. The reactivity of such compounds toward various mono- and dinucleophilic reagents is considered. The potential of these compounds for synthesis of different acyclic, carbo- and heterocyclic molecules is demonstrated. Special attention is paid to the practical use of 2-(1-alkoxyalkylidene)-1,3-dicarbonyl compounds and their derivatives, which are of interest in medicine and for design of new materials.

The bibliography includes 226 references.

References

1.
Fluorine-containing β-Diketones
Pashkevich K.I., Saloutin V.I., Postovskii I.Y.
Russian Chemical Reviews , 1981
2.
Fluorine-containing β-Ketoesters
Pashkevich K.I., Saloutin V.I.
Russian Chemical Reviews , 1985
3.
α-Hydroxylation of β-Dicarbonyl Compounds
Christoffers J., Baro A., Werner T.
Advanced Synthesis and Catalysis , 2004
4.
Aromatic compounds as synthons for 1,3-dicarbonyl derivatives
Hilt G., Weske D.F.
Chemical Society Reviews , 2009
5.
Asymmetric transformations involving 1,2-dicarbonyl compounds as pronucleophiles
Raimondi W., Bonne D., Rodriguez J.
Chemical Communications , 2012
7.
β-Diketo Building Blocks for MCRs-Based Syntheses of Heterocycles
del Duque M.M., Allais C., Isambert N., Constantieux T., Rodriguez J.
Topics in Heterocyclic Chemistry , 2010
8.
1,3-Dicarbonyl compounds in stereoselective domino and multicomponent reactions
Bonne D., Coquerel Y., Constantieux T., Rodriguez J.
Tetrahedron Asymmetry , 2010
9.
Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions
Simon C., Constantieux T., Rodriguez J.
European Journal of Organic Chemistry , 2004
11.
2-(Het)arylhydrazono-1,3-dicarbonyl compounds in organic synthesis
Shchegolkov E.V., Burgart Y.V., Khudina O.G., Saloutin V.I., Chupakhin O.N.
Russian Chemical Reviews , 2010
12.
Fluorinated azines and benzazines containing oxygen or sulfur atoms
Nosova E.V., Lipunova G.N., Charushin V.N., Chupakhin O.N.
Journal of Fluorine Chemistry , 2010
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
Synthesis of diversely fluorinated pyrazoles as novel active agrochemical ingredients
Giornal F., Pazenok S., Rodefeld L., Lui N., Vors J., Leroux F.R.
Journal of Fluorine Chemistry , 2013
16.
Recent advances in the chemistry of α,β-unsaturated trifluoromethylketones
Druzhinin S.V., Balenkova E.S., Nenajdenko V.G.
Tetrahedron , 2007
17.
Chemistry of 2-Acylcycloalkane-1,3-diones
Rubinov D.B., Rubinova I.L., Akhrem A.A.
Chemical Reviews , 1999
18.
Reactions of Orthoesters with Active Methylene Compounds
Jones R.G.
Journal of the American Chemical Society , 1952
19.
Synthesis and structure of 2-ethoxy- and 2-aminomethylidene-3-fluoroalkyl-3-oxopropionates
Pryadeina M.V., Burgart Y.V., Saloutin V.I., Slepukhin P.A., Kazheva O.N., Shilov G.V., D’yachenko O.A., Chupakhin O.N.
Russian Journal of Organic Chemistry , 2007
20.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
21.
Juranić I., Husinec S., Savić V., Porter A.E.
Collection of Czechoslovak Chemical Communications , 2009
22.
23
N. V. Vostrilova
Dokl. Akad. Nauk Uzbek. SSR , 1958
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
24.
Novel fluorinated chromones
Saloutin V.I., Skryabina Z.E., Bazyl' I.T., Chupakhin O.N.
Journal of Fluorine Chemistry , 1993
27.
Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives.
NAITO H., SUGIMORI M., MITSUI I., NAKAMURA Y., IWAHANA M., ISHII M., HIROTANI K., KUMAZAWA E., EJIMA A.
Chemical and Pharmaceutical Bulletin , 2011
28.
Inhibitors of NF-κB and AP-1 Gene Expression:  SAR Studies on the Pyrimidine Portion of 2-Chloro-4-trifluoromethylpyrimidine-5-[N-(3‘,5‘-bis(trifluoromethyl)phenyl)carboxamide]
Palanki M.S., Erdman P.E., Gayo-Fung L.M., Shevlin G.I., Sullivan R.W., Goldman M.E., Ransone L.J., Bennett B.L., Manning A.M., Suto M.J.
Journal of Medicinal Chemistry , 2000
29.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
30.
31
A. A. Krasnovskii
Biokhimiya , 1960
31.
1H-Pyrazolo[3,4-b]pyridine Inhibitors of Cyclin-Dependent Kinases
Misra R.N., Rawlins D.B., Xiao H., Shan W., Bursuker I., Kellar K.A., Mulheron J.G., Sack J.S., Tokarski J.S., Kimball S.D., Webster K.R.
Bioorganic and Medicinal Chemistry Letters , 2003
32.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
33.
34
G. W. Robinson
J. Chem. Phys. , 1886
34.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
35.
36
J. Billon
Bull. Soc. chim. France , 1960
36.
Novel Thiazole-Based Heterocycles as Selective Inhibitors of Fibrinogen-Mediated Platelet Aggregation
Sanfilippo P.J., Andrade-Gordon P., Urbanski M.J., Beers K.N., Eckardt A., Falotico R., Ginsberg M.H., Offord S., Press J.B.
Journal of Medicinal Chemistry , 1995
37.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
38.
39
V. F. Gachkovskii
Biofizika , 1959
39.
A new synthesis of 7H-pyrido(1,2,3-de)(1,4)benzoxazine derivatives including an antibacterial agent, ofloxacin.
EGAWA H., MIYAMOTO T., MATSUMOTO J.
Chemical and Pharmaceutical Bulletin , 2011
41.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
42.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
43.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
44.
45
W. Hendrich
Roczniki Chemii , 1958
45.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
46.
47
G. Oster
"Research in Photosynthesis" , 1957
47.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
48.
Ethyl 5-oxo-2,5-dihydro-4-isoxazolecarboxylate hydroxylamine salt
Kennedy A.R., Khalaf A.I., Suckling C.J., Waigh R.D.
Acta Crystallographica Section E Structure Reports Online , 2003
49.
Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α2C-Adrenoceptor Antagonists
Höglund I.P., Silver S., Engström M.T., Salo H., Tauber A., Kyyrönen H., Saarenketo P., Hoffrén A., Kokko K., Pohjanoksa K., Sallinen J., Savola J., Wurster S., Kallatsa O.A.
Journal of Medicinal Chemistry , 2006
50.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
51.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
52.
Chemical synthesis and biological activities of 5-deazaaminopterin analogs bearing substituent(s) at the 5- and/or 7-position(s)
Su T.L., Huang J.T., Chou T.C., Otter G.M., Sirotnak F.M., Watanabe K.A.
Journal of Medicinal Chemistry , 1988
53.
54
R. Livingston
J. Phys. Chem. , 1941
54.
55
G. A. Bogdanovskii
1958
55.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
56.
57
R. Livingston
"Research in Photosynthesis" , 1957
57.
A convenient synthesis of13C4-Leflunomide and its primary metabolite13C4-A77 1726
Faragher R.J., Motto J.M., Kaminski M.A., Schwan A.L.
Journal of Labelled Compounds and Radiopharmaceuticals , 2003
58.
59
H. Linshitz
"Research in Photosynthesis" , 1957
59.
60
A. N. Terenin
Optika i Spektrosk. , 1956
60.
61
A. N. Terenin
1959
61.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
62.
A novel series of piperazinyl-pyridine ureas as antagonists of the purinergic P2Y12 receptor
Bach P., Boström J., Brickmann K., van Giezen J.J., Hovland R., Petersson A.U., Ray A., Zetterberg F.
Bioorganic and Medicinal Chemistry Letters , 2011
64.
65
A. A. Krasnovskii
Biofizika , 1959
65.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
66.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
67.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1946
70.
Diversity-oriented synthesis of 1-hydroxy-2,4-benzodioates by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-alkoxy- and 3-silyloxy-2-alkoxycarbonyl-2-en-1-ones
Shkoor M., Riahi A., Fatunsin O., Hussain I., Yawer M.A., Lubbe M., Reim S., Reinke H., Fischer C., Langer P.
Organic and Biomolecular Chemistry , 2009
74.
Solvent‐Free Microwave Michael Addition Between EMME and Various Nucleophiles
Loupy A., Song S.J., Cho S.J., Park D.K., Kwon T.W.
Synthetic Communications , 2005
75.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
76.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
77.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
78.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
79.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
80.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
81.
Synthesis and evaluation of novel pyrimidine-based dual EGFR/Her-2 inhibitors
Suzuki N., Shiota T., Watanabe F., Haga N., Murashi T., Ohara T., Matsuo K., Oomori N., Yari H., Dohi K., Inoue M., Iguchi M., Sentou J., Wada T.
Bioorganic and Medicinal Chemistry Letters , 2011
82.
Evaluation of secondary amide replacements in a series of CCR5 antagonists as a means to increase intrinsic membrane permeability. Part 1: Optimization of gem-disubstituted azacycles
Lemoine R.C., Petersen A.C., Setti L., Wanner J., Jekle A., Heilek G., deRosier A., Ji C., Berry P., Rotstein D.
Bioorganic and Medicinal Chemistry Letters , 2010
83.
Oximino-piperidino-piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides.
Palani A., Shapiro S., Clader J.W., Greenlee W.J., Vice S., McCombie S., Cox K., Strizki J., Baroudy B.M.
Bioorganic and Medicinal Chemistry Letters , 2003
84.
Piperazine-based CCR5 antagonists as HIV-1 inhibitors. III: synthesis, antiviral and pharmacokinetic profiles of symmetrical heteroaryl carboxamides
McCombie S.W., Tagat J.R., Vice S.F., Lin S., Steensma R., Palani A., Neustadt B.R., Baroudy B.M., Strizki J.M., Endres M., Cox K., Dan N., Chou C.
Bioorganic and Medicinal Chemistry Letters , 2003
85.
86
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
86.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
87.
Intermolecular Methoxycarbonylation of Terminal Alkynes Catalyzed by Palladium(II) Bis(oxazoline) Complexes
Kato K., Motodate S., Mochida T., Kobayashi T., Akita H.
Angewandte Chemie - International Edition , 2009
88.
Synthesis of the Alkaloids (±)-Deplancheine and Flavopereirine
S. Venkatachalam G., Jai Sankar P., K. Das S.
Heterocycles , 1991
89.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
90.
91
L. M. Vorob'eva
Biokhimiya , 1956
91.
Highly stereoselective total synthesis of .beta.-ribofuranosylmalonate
Katagiri N., Akatsuka H., Haneda T., Kaneko C., Sera A.
Journal of Organic Chemistry , 1988
93.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
94.
CERIC(IV) AMMONIUM NITRATE MEDIATED TRANSESTERIFICATION AND ESTERIFICATION
Štefane B., Kočevar M., Polanc S.
Synthetic Communications , 2002
95.
10.1002/(SICI)1097-458X(199707)35:7<432::AID-OMR107>3.0.CO;2-F
96.
2,5-Dihydropyrazolo[4,3-c]pyridin-3-ones: functionally selective benzodiazepine binding site ligands on the GABAA receptor
Mitchinson A., Atack J.R., Blurton P., Carling R.W., Castro J.L., Curley K.S., N. Russell M.G., Marshall G., McKernan R.M., Moore K.W., Narquizian R., Smith A., Street L.J., Thompson S., Wafford K., et. al.
Bioorganic and Medicinal Chemistry Letters , 2004
99.
Synthesis, Potency, and In Vivo Profiles of Quinoline Containing Histamine H3 Receptor Inverse Agonists
Altenbach R.J., Liu H., Banfor P.N., Browman K.E., Fox G.B., Fryer R.M., Komater V.A., Krueger K.M., Marsh K., Miller T.R., Pan J.B., Pan L., Sun M., Thiffault C., Wetter J., et. al.
Journal of Medicinal Chemistry , 2007
100.
Synthesis and complexing ability of 2-(2-ethoxycarbonyl-3-oxo-3-polyfluoroalkylprop-1-enylamino) benzoic acids
Kudyakova Y.S., Goryaeva M.V., Burgart Y.V., Saloutin V.I., Slepukhin P.A.
Russian Chemical Bulletin , 2009
101.
102
F. Fichter
Helv. Chim. Acta , 1922
102.
New enamine ligands derived from ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates and o-phenylenediamine
Kudyakova Y.S., Goryaeva M.V., Burgart Y.V., Slepukhin P.A., Saloutin V.I.
Russian Chemical Bulletin , 2010
103.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
104.
Synthesis and properties of water-soluble 2-aminomethylidene derivatives of 1,3-dicarbonyl compounds
Bazhin D.N., Kudyakova Y.S., Gorbunova T.I., Burgart Y.V., Zapevalov A.Y., Saloutin V.I.
Russian Journal of General Chemistry , 2013
105.
106
F. Fichter
Helv. Chim. Acta , 1927
106.
4-Quinolone Derivatives:  High-Affinity Ligands at the Benzodiazepine Site of Brain GABAA Receptors. Synthesis, Pharmacology, and Pharmacophore Modeling
Lager E., Andersson P., Nilsson J., Pettersson I., Nielsen E.Ø., Nielsen M., Sterner O., Liljefors T.
Journal of Medicinal Chemistry , 2006
107.
Design, synthesis, and biological evaluation of novel 4-hydro-quinoline-3-carboxamide derivatives as an immunomodulator
He J., Yun L., Yang R., Xiao Z., Cheng J., Zhou W., Zhang Y.
Bioorganic and Medicinal Chemistry Letters , 2005
108.
Synthesis and SAR of bicyclic heteroaryl hydroxamic acid MMP and TACE inhibitors
Zask A., Gu Y., Albright J.D., Du X., Hogan M., Levin J.I., Chen J.M., Killar L.M., Sung A., DiJoseph J.F., Sharr M.A., Roth C.E., Skala S., Jin G., Cowling R., et. al.
Bioorganic and Medicinal Chemistry Letters , 2003
109.
Solvent-free Synthesis of Quinolone Derivatives
Milata V., Loupy A., Vo-Thanh G., Černuchová P.
Heterocycles , 2004
110.
Route to a Family of Robust, Non-interpenetrated Metal-Organic Frameworks with pto-like Topology
Klein N., Senkovska I., Baburin I.A., Grünker R., Stoeck U., Schlichtenmayer M., Streppel B., Mueller U., Leoni S., Hirscher M., Kaskel S.
Chemistry - A European Journal , 2011
111.
Synthesis and anticancer activities of some novel 2-(benzo[d]thiazol-2-yl)-8-substituted-2H-pyrazolo[4,3-c]quinolin-3(5H)-ones
Reis R.D., Azevedo E.C., de Souza M.C., Ferreira V.F., Montenegro R.C., Araújo A.J., Pessoa C., Costa-Lotufo L.V., de Moraes M.O., Filho J.D., de Souza A.M., de Carvalho N.C., Castro H.C., Rodrigues C.R., Vasconcelos T.R., et. al.
European Journal of Medicinal Chemistry , 2011
112.
Investigating the Role of Metal Chelation in HIV-1 Integrase Strand Transfer Inhibitors
Bacchi A., Carcelli M., Compari C., Fisicaro E., Pala N., Rispoli G., Rogolino D., Sanchez T.W., Sechi M., Sinisi V., Neamati N.
Journal of Medicinal Chemistry , 2011
113.
Design and Synthesis of Potent Inhibitors of the Malaria Parasite Dihydroorotate Dehydrogenase
Heikkilä T., Ramsey C., Davies M., Galtier C., Stead A.M., Johnson A.P., Fishwick C.W., Boa A.N., McConkey G.A.
Journal of Medicinal Chemistry , 2006
114.
Tautomerism and Acidity in 41Quinolone-3Xarboxylic Acid Derivatives
de la Cruz A., Elguero J., Goya P., Martínez A., Pfleiderer W.
Tetrahedron , 1992
116.
Evaluation of 3-Carboxy-4(1H)-quinolones as Inhibitors of Human Protein Kinase CK2
Golub A.G., Yakovenko O.Y., Bdzhola V.G., Sapelkin V.M., Zien P., Yarmoluk S.M.
Journal of Medicinal Chemistry , 2006
118.
Pharmacomodulations around the 4-Oxo-1,4-dihydroquinoline-3-carboxamides, a Class of Potent CB2-Selective Cannabinoid Receptor Ligands:  Consequences in Receptor Affinity and Functionality
Stern E., Muccioli G.G., Bosier B., Hamtiaux L., Millet R., Poupaert J.H., Hénichart J., Depreux P., Goossens J., Lambert D.M.
Journal of Medicinal Chemistry , 2007
119.
Design, synthesis and docking studies of new quinoline-3-carbohydrazide derivatives as antitubercular agents
Thomas K.D., Adhikari A.V., Telkar S., Chowdhury I.H., Mahmood R., Pal N.K., Row G., Sumesh E.
European Journal of Medicinal Chemistry , 2011
120.
Syntheses of quinolone hydrochloride enantiomers from synthons (R)- and (S)-2-methylpiperazine
Liu B., Yang C., Xu G., Zhu Y., Cui J., Wu X., Xie Y.
Bioorganic and Medicinal Chemistry , 2005
121.
Synthesis and antibacterial evaluation of novel 8-fluoro Norfloxacin derivatives as potential probes for methicillin and vancomycin-resistant Staphylococcus aureus
Sunduru N., Gupta L., Chauhan K., Mishra N.N., Shukla P.K., Chauhan P.M.
European Journal of Medicinal Chemistry , 2011
122.
Synthesis and structure–activity relationship for new series of 4-Phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase
Kubo K., Ohyama S., Shimizu T., Takami A., Murooka H., Nishitoba T., Kato S., Yagi M., Kobayashi Y., Iinuma N., Isoe T., Nakamura K., Iijima H., Osawa T., Izawa T., et. al.
Bioorganic and Medicinal Chemistry , 2003
123.
Identification of Potent and Selective Inhibitors of PDGF Receptor Autophosphorylation
Furuta T., Sakai T., Senga T., Osawa T., Kubo K., Shimizu T., Suzuki R., Yoshino T., Endo M., Miwa A.
Journal of Medicinal Chemistry , 2006
124.
Microwave Activated Solid Support Synthesis of New Antibacterial Quinolones
Kidwai M., Misra P., Dave B., Bhushan K.R., Saxena R.K., Singh M.
Monatshefte fur Chemie , 2000
125.
Heterocyclization of Functionalized Vinylic Derivatives of Imidazo[1,2-a]pyridines
Chezal J.M., Moreau E., Delmas G., Gueiffier A., Blache Y., Grassy G., Lartigue C., Chavignon O., Teulade J.C.
Journal of Organic Chemistry , 2001
126.
127
R. Pasternak
Helv. Chim. Acta , 1948
127.
128
J. Wiemann
Bull. Soc. chim. France , 1952
128.
Novel HIV-1 Integrase Inhibitors Derived from Quinolone Antibiotics
Sato M., Motomura T., Aramaki H., Matsuda T., Yamashita M., Ito Y., Kawakami H., Matsuzaki Y., Watanabe W., Yamataka K., Ikeda S., Kodama E., Matsuoka M., Shinkai H.
Journal of Medicinal Chemistry , 2006
129.
Synthesis and pharmacology of pyrido[2,3-d]pyrimidinediones bearing polar substituents as adenosine receptor antagonists
Bulicz J., Bertarelli D.C., Baumert D., Fülle F., Müller C.E., Heber D.
Bioorganic and Medicinal Chemistry , 2006
131.
Optimization of a Potent, Orally Active S1P1 Agonist Containing a Quinolinone Core
Harrington P.E., Croghan M.D., Fotsch C., Frohn M., Lanman B.A., Pennington L.D., Pickrell A.J., Reed A.B., Sham K.K., Tasker A., Arnett H.A., Fiorino M., Lee M.R., McElvain M., Morrison H.G., et. al.
ACS Medicinal Chemistry Letters , 2011
132.
Novel amino-piperidines as potent antibacterials targeting bacterial type IIA topoisomerases
Miles T.J., Axten J.M., Barfoot C., Brooks G., Brown P., Chen D., Dabbs S., Davies D.T., Downie D.L., Eyrisch S., Gallagher T., Giordano I., Gwynn M.N., Hennessy A., Hoover J., et. al.
Bioorganic and Medicinal Chemistry Letters , 2011
134.
Synthesis and evaluation of quinoline carboxyguanidines as antidiabetic agents
Edmont D., Rocher R., Plisson C., Chenault J.
Bioorganic and Medicinal Chemistry Letters , 2000
135.
Further modification on phenyl acetic acid based quinolines as liver X receptor modulators
Hu B., Jetter J., Kaufman D., Singhaus R., Bernotas R., Unwalla R., Quinet E., Savio D., Halpern A., Basso M., Keith J., Clerin V., Chen L., Liu Q., Feingold I., et. al.
Bioorganic and Medicinal Chemistry , 2007
136.
Discovery of Phenyl Acetic Acid Substituted Quinolines as Novel Liver X Receptor Agonists for the Treatment of Atherosclerosis
Hu B., Collini M., Unwalla R., Miller C., Singhaus R., Quinet E., Savio D., Halpern A., Basso M., Keith J., Clerin V., Chen L., Resmini C., Liu Q., Feingold I., et. al.
Journal of Medicinal Chemistry , 2006
137.
Nucleophilic Vinylic Substitution (SNV) of Activated Alkoxymethylene Derivatives with 6-Aminoquinoxaline
Saloň J., Milata V., Gatial A., Prónayová N., Leško J., Černuchová P., Rappoport Z., Vo-Thanh G., Loupy A.
European Journal of Organic Chemistry , 2005
138.
Saloň J., Milata V., Prónayová N., Leško J.
Collection of Czechoslovak Chemical Communications , 2002
139.
Inhibition of the Signal Transducer and Activator of Transcription-3 (STAT3) Signaling Pathway by 4-Oxo-1-Phenyl-1,4-Dihydroquinoline-3-Carboxylic Acid Esters
Xu J., Cole D.C., Chang C.B., Ayyad R., Asselin M., Hao W., Gibbons J., Jelinsky S.A., Saraf K.A., Park K.
Journal of Medicinal Chemistry , 2008
140.
Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation
Dinakaran M., Senthilkumar P., Yogeeswari P., China A., Nagaraja V., Sriram D.
Bioorganic and Medicinal Chemistry Letters , 2008
141.
Study on the Synthesis and Cytotoxicity of New Quinophenoxazine Derivatives
Kwon Y., Na Y.
Chemical and Pharmaceutical Bulletin , 2006
143.
Synthesis, biological evaluation and molecular modeling studies of quinolonyl diketo acid derivatives: New structural insight into the HIV-1 integrase inhibition
Vandurm P., Guiguen A., Cauvin C., Georges B., Le Van K., Michaux C., Cardona C., Mbemba G., Mouscadet J., László Hevesi, Van Lint C., Wouters J.
European Journal of Medicinal Chemistry , 2011
144.
Novel Bifunctional Quinolonyl Diketo Acid Derivatives as HIV-1 Integrase Inhibitors:  Design, Synthesis, Biological Activities, and Mechanism of Action
Di Santo R., Costi R., Roux A., Artico M., Lavecchia A., Marinelli L., Novellino E., Palmisano L., Andreotti M., Amici R., Galluzzo C.M., Nencioni L., Palamara A.T., Pommier Y., Marchand C., et. al.
Journal of Medicinal Chemistry , 2006
146.
10.1002/1521-3765(20010518)7:10<2143::AID-CHEM2143>3.0.CO;2-D
147.
Synthesis, Properties, and Reactions of 5-Substituted Derivatives of 2,3-Diphenylquinoxaline [1]
Saloň J., Milata V., Chudík M., Prónayová N., Leško J., Seman M., Belicová A.
Monatshefte fur Chemie , 2003
148.
Synthesis and structure–activity relationships of antimalarial 4-oxo-3-carboxyl quinolones
Zhang Y., Guiguemde W.A., Sigal M., Zhu F., Connelly M.C., Nwaka S., Guy R.K.
Bioorganic and Medicinal Chemistry , 2010
150.
Synthesis and Magnetic Properties of New Octahedral Iron(II) Complexes
Weber B., Kaps E., Obel J., Bauer W.
Zeitschrift fur Anorganische und Allgemeine Chemie , 2008
151.
Cooperative Iron(II) Spin Crossover Complexes with N4O2 Coordination Sphere
Weber B., Kaps E., Weigand J., Carbonera C., Létard J., Achterhold K., Parak F.G.
Inorganic Chemistry , 2007
152.
Synthesis and Characterisation of Two New Iron(II) Spin‐Crossover Complexes with N 4 O 2 Coordination Spheres – Optimizing Preconditions for Cooperative Interactions
Weber B., Kaps E.S., Desplanches C., Létard J., Achterhold K., Parak F.G.
European Journal of Inorganic Chemistry , 2008
153.
Two New Iron(II) Spin‐Crossover Complexes with N 4 O 2 Coordination Sphere and Spin Transition around Room Temperature
Weber B., Obel J., Henner‐Vásquez D., Bauer W.
European Journal of Inorganic Chemistry , 2009
155.
Cooperative spin transition in a lipid layer like system
Schlamp S., Weber B., Naik A.D., Garcia Y.
Chemical Communications , 2011
156.
New tetradentate N2O2-ligands based on 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates and ethylenediamine
Kudyakova Y.S., Goryaeva M.V., Burgart Y.V., Saloutin V.I.
Russian Journal of Organic Chemistry , 2010
157.
158
Friedl.
158.
New chiral metal complexes based on 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates
Kudyakova Y.S., Goryaeva M.V., Burgart Y.V., Saloutin V.I.
Russian Journal of Organic Chemistry , 2011
159.
160
1912
160.
Quinolone Carboxylic Acids as a Novel Monoketo Acid Class of Human Immunodeficiency Virus Type 1 Integrase Inhibitors
Sato M., Kawakami H., Motomura T., Aramaki H., Matsuda T., Yamashita M., Ito Y., Matsuzaki Y., Yamataka K., Ikeda S., Shinkai H.
Journal of Medicinal Chemistry , 2009
161.
Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors
Hamblin J.N., Angell T.D., Ballantine S.P., Cook C.M., Cooper A.W., Dawson J., Delves C.J., Jones P.S., Lindvall M., Lucas F.S., Mitchell C.J., Neu M.Y., Ranshaw L.E., Solanke Y.E., Somers D.O., et. al.
Bioorganic and Medicinal Chemistry Letters , 2008
162.
The identification a novel, selective, non-steroidal, functional glucocorticoid receptor antagonist
Rimland J., Dunne A., Hunjan S.S., Sasse R., Uings I., Montanari D., Caivano M., Shah P., Standing D., Gray D., Brown D., Cairns W., Trump R., Smith P.W., Bertheleme N., et. al.
Bioorganic and Medicinal Chemistry Letters , 2010
163.
Efficient and Practical Synthesis of Dissymmetrical Ethers of 4-Nitrocatechol
Subashini M., Balasubramanian K.K., Bhagavathy S.
Synthetic Communications , 2008
164.
Identification of 3-amido-4-anilinoquinolines as potent and selective inhibitors of CSF-1R kinase
Scott D.A., Balliet C.L., Cook D.J., Davies A.M., Gero T.W., Omer C.A., Poondru S., Theoclitou M., Tyurin B., Zinda M.J.
Bioorganic and Medicinal Chemistry Letters , 2009
165.
Novel Synthesis and Structural Characterization of a High-Affinity Paramagnetic Kinase Probe for the Identification of Non-ATP Site Binders by Nuclear Magnetic Resonance
Moy F.J., Lee A., Gavrin L.K., Xu Z.B., Sievers A., Kieras E., Stochaj W., Mosyak L., McKew J., Tsao D.H.
Journal of Medicinal Chemistry , 2009
166.
C–C recyclizations of some 2,7-disubstituted 6-ethoxycarbonylpyrazolo[1,5-a]pyrimidines
Danagulyan G.G., Boyakhchyan A.P., Danagulyan A.G., Panosyan H.A.
Chemistry of Heterocyclic Compounds , 2011
167.
168
1918
168.
Discovery of pyrazolopyrimidines as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A
Shen H.C., Taggart A.K., Wilsie L.C., Waters M.G., Hammond M.L., Tata J.R., Colletti S.L.
Bioorganic and Medicinal Chemistry Letters , 2008
169.
Indazolylpyrazolopyrimidine as Highly Potent B-Raf Inhibitors with in Vivo Activity
Wang X., Berger D.M., Salaski E.J., Torres N., Dutia M., Hanna C., Hu Y., Levin J.I., Powell D., Wojciechowicz D., Collins K., Frommer E., Lucas J.
Journal of Medicinal Chemistry , 2010
171.
Recyclization of Condensed Carbethoxypyrimidines Accompanied by Substitution of a Carbon Atom into the Heterocycle
Danagulyan G.G., Mkrtchyan A.D., Panosyan G.A.
Chemistry of Heterocyclic Compounds , 2005
172.
173
Friedl.
173.
2-R-7-methyl[1,2,4]triazolo[2,3-a]pyrimidines: synthesis and structures
Shikhaliev K.S., Krylski D.V., Potapov A.Y., Nefedov S.E., Sidorenko O.E.
Russian Chemical Bulletin , 2008
174.
175
I. Mayer
1966
176.
On triazoles.XXXV. The reaction of 5-amino-1,2,4-triazoles with di- and triketones
Reiter J., Pongó L., Kövesdi I., Pallagi I.
Journal of Heterocyclic Chemistry , 1995
177.
178
1946
178.
Pryadeina Marina Valer'evna, Burgart Yanina Valer'evna, Saloutin Viktor Ivanovich, Chupakhin Oleg Nikolaevich
Mendeleev Communications , 2008
179.
Synthesis of Fluoroalkylated Dihydroazolo[1,5-a]pyrimidines and Their Ring-Chain Isomerism
V. Goryaeva M., V. Burgart Y., I. Saloutin V., V. Sadchikova E., N. Ulomskii E.
Heterocycles , 2009
180.
Synthesis of pyrimido[1,2-a]benzimidazoles from ethyl 2-ethoxymethylidene-3-oxo-3-(polyfluoroalkyl)propionates
Goryaeva M.V., Burgart Y.V., Saloutin V.I.
Russian Journal of Organic Chemistry , 2010
183.
185
1954
184.
186
Chem. Abs. , 1956
185.
187
1954
186.
188
Chem. Abs. , 1955
187.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
188.
190
H. Law
J. Chem. Soc. , 1912
189.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
190.
192
E. Pannain
Rend. Classe Sci. fis. mat. nat. (5) , 1908
192.
194
A. A. Vertman
"Svoistva Rasplavov Zheleza" (Properties of Iron Melts) , 1969
193.
5-Iodo-3-Ethoxypyrazoles: An Entry Point to New Chemical Entities
Guillou S., Janin Y.
Chemistry - A European Journal , 2010
194.
196
E. Müller
Z. Elektrochem. , 1910
195.
197
J. Sicher
Chem. Listy , 1955
196.
“Reported, but Still Unknown.” A Closer Look into 3,4-Bis- and 3,4,5-Tris(trifluoromethyl)pyrazoles
Gerus I.I., Mironetz R.X., Kondratov I.S., Bezdudny A.V., Dmytriv Y.V., Shishkin O.V., Starova V.S., Zaporozhets O.A., Tolmachev A.A., Mykhailiuk P.K.
Journal of Organic Chemistry , 2011
197.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
198.
200
Ref. Zh. Khim. , 1975
200.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
201.
203
L. Andrieux
Compt. rend. , 1929
202.
204
Cherkesov A I
Ref. Zh. Khim. , 1968
203.
SYNTHESIS OF 4-ACETYL (OR CARBETHOXY) -5-METHYL- 1-HETEROCYCLYLPYRAZOLES
Singh S.Ρ., Kapoor J.Κ., Sadana A.Κ.
Heterocyclic Communications , 2001
204.
Synthesis and Antitumor Activity of Novel Pyrimidinyl Pyrazole Derivatives. III. Synthesis and Antitumor Activity of 3-Phenylpiperazinyl-1-trans-propenes
Naito H., Ohsuki S., Atsumi R., Minami M., Mochizuki M., Hirotani K., Kumazawa E., Ejima A.
Chemical and Pharmaceutical Bulletin , 2005
205.
207
F. Fichter
"Organische Elektrochemie" , 1942
206.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
207.
Microwave-Assisted and Continuous Flow Multistep Synthesis of 4-(Pyrazol-1-yl)carboxanilides
Obermayer D., Glasnov T.N., Kappe C.O.
Journal of Organic Chemistry , 2011
208.
Regioselective cyclocondensation of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with thiazolylhydrazines
Pryadeina M.V., Denisova A.B., Burgart Y.V., Saloutin V.I.
Russian Journal of Organic Chemistry , 2008
211.
214
L. V. Pavlova
1965
212.
215
N. D. Tomashov
Zh. Prikl. Khim. , 1970
213.
216
A. P. Tomilov
Zhur. Prikl. Khim. , 1959
214.
217
1925
215.
218
Chem. Zentr. II , 1925
216.
219
G. I. Pustoshkin
Collected Papers "Biologicheskie Aktivnie Soedinenii" (Biologically Active Compounds) , 1955
217.
220
K. Ziegler
Angew. Chem. , 1955
218.
Reactions of 3-ethoxymethylidenepentane-2,4-dione and ethyl 2-ethoxymethylidene-3-oxobutanoate with benzohydrazide
Yakimovich S.I., Zerova I.V., Pakal’nis V.V.
Russian Journal of Organic Chemistry , 2008
219.
Design, Synthesis, and Biological Evaluation of a Library of 1-(2-Thiazolyl)-5-(trifluoromethyl)pyrazole-4-carboxamides
Donohue B.A., Michelotti E.L., Reader J.C., Reader V., Stirling M., Tice C.M.
Journal of Combinatorial Chemistry , 2001
220.
225
1960
221.
226
Chem. Abs. , 1961
222.
Synthesis of Fluorinated 1,3,4-Oxadiazino[6,5,4-i,j]quinolines
Lipunova G.N., Nosova E.V., Charushin V.N., Chasovskikh O.M.
Chemistry of Heterocyclic Compounds , 2001
223.
228
B. Roetheke
Chem. Abs. , 1959
224.
Synthesis of New Fluorinated Derivatives of Quinolinecarboxylic Acids
Nosova E.V., Sidorova L.P., Lipunova G.N., Mochul'skaya N.N., Chasovskikh O.M., Charushin V.N.
Chemistry of Heterocyclic Compounds , 2002
225.
230
Chem. Abs. , 1962
226.
1,2,4-Triazino[5,6,1-i,j]quinolines: a new type of tricyclic analogs of fluoroquinolones
Lipunova G.N., Nosova E.V., Mochul"skaya N.N., Andreiko A.A., Chasovskikh O.M., Charushin V.N.
Russian Chemical Bulletin , 2002
227.
232
Chem. Abs. , 1960
229.
234
Ebach E A
Chem. Abs. , 1966
230.
235
R. Peffen
1967
231.
236
P. Peshev
Rev. internat. hautes Temperat. et Réfract. , 1969
232.
Synthesis and Heterocyclizations of 3,4-Dihydroquinazolin-2-yl Guanidine in the Search of New Anticancer Agents
Keung Chui W., V. Dolzhenko A., V. Dolzhenko A., Chelle Foo M., Jen Tan B., Ngar Chee Chiu G.
Heterocycles , 2009
233.
Discovery and Structure−Activity Relationships of Trisubstituted Pyrimidines/Pyridines as Novel Calcium-Sensing Receptor Antagonists
Yang W., Ruan Z., Wang Y., Van Kirk K., Ma Z., Arey B.J., Cooper C.B., Seethala R., Feyen J.H., Dickson J.K.
Journal of Medicinal Chemistry , 2009
234.
Synthesis of 4-unsubstituted dihydropyrimidines. Nucleophilic substitution at position-2 of dihydropyrimidines
Cho H., Nishimura Y., Yasui Y., Kobayashi S., Yoshida S., Kwon E., Yamaguchi M.
Tetrahedron , 2011
236.
Isomerization/recyclization of some 5-ethoxycarbonyl-pyrimidines
Vardanyan R.S., Hruby V.J., Danagulyan G.G., Mkrtchyan A.D.
Journal of Heterocyclic Chemistry , 2005
238.
243
G. A. Kudintseva
1958
239.
244
C. Wilson
Record. Chem. Prog. , 1949
243.
4-Oxo-4H-quinolizine-3-carboxylic Acids as Mg2+ Selective, Fluorescent Indicators
Otten P.A., London R.E., Levy L.A.
Bioconjugate Chemistry , 2001
244.
Quinolizidinone carboxylic acid selective M1 allosteric modulators: SAR in the piperidine series
Kuduk S.D., Chang R.K., Di Marco C.N., Ray W.J., Ma L., Wittmann M., Seager M.A., Koeplinger K.A., Thompson C.D., Hartman G.D., Bilodeau M.T.
Bioorganic and Medicinal Chemistry Letters , 2011
245.
250
D. Goerrig
1955
246.
Solid-Phase Synthesis of 5-Biphenyl-2-yl-1H-tetrazoles
Kivrakidou O., Bräse S., Hülshorst F., Griebenow N.
Organic Letters , 2004
247.
Discovery of a Potent, Selective, and Orally Efficacious Pyrimidinooxazinyl Bicyclooctaneacetic Acid Diacylglycerol Acyltransferase-1 Inhibitor
Birch A.M., Birtles S., Buckett L.K., Kemmitt P.D., Smith G.J., Smith T.J., Turnbull A.V., Wang S.J.
Journal of Medicinal Chemistry , 2009
248.
A regioselective synthesis of 2,4-dialkyl resorcinols
Ceglia S.S., Kress M.H., Nelson T.D., McNamara J.M.
Tetrahedron Letters , 2005
249.
New Method of Synthesis of 5-Acetyl-3-cyano-6-methylpyridine-2(1H)-Thione and Its Properties
Yakunin Y.Y., Dyachenko V.D., Litvinov V.P.
Chemistry of Heterocyclic Compounds , 2001
250.
255
Tomita M
Chem. Abs. , 1939
252.
257
L. Ya. Markovskii
Zh. Neorg. Khim. , 1957
253.
Gorobets N.Y., Tkachova V.P., Tkachov R.P., Dyachenko O.D., Rusanov E.B., Dyachenko V.D.
Arkivoc , 2010
254.
New approach to CF3-containing polysubstituted anilines: reaction of β-trifluoroacetylvinyl ethers with enamines
Volochnyuk D.M., Kostyuk A.N., Sibgatulin D.A., Chernega A.N., Pinchuk A.M., Tolmachev A.A.
Tetrahedron , 2004
255.
Novel approach to the synthesis of 1,3-diazapyrenes
Aksenov A.V., Borovlev I.V., Aksenova I.V., Lobach D.A., Lyakhovnenko A.S.
Chemistry of Heterocyclic Compounds , 2009
256.
261
C. Friedel
Ann. Chim. Phys. , 1876
258.
4-Nitrobenzodifuroxan: a highly reactive nitroolefin in Diels–Alder reactions
Kurbatov S., Goumont R., Lakhdar S., Marrot J., Terrier F.
Tetrahedron , 2005
259.
Synthese De 2-Amino-4-Phosphono-4H-Pyranes
Gaied L.B., Zantour H.
Phosphorus, Sulfur and Silicon and the Related Elements , 2000
261.
Reversible inhibitors of the gastric (H+/K+)-ATPase. 2. 1-Arylpyrrolo[3,2-c]quinolines: effect of the 4-substituent
Leach C.A., Brown T.H., Ife R.J., Keeling D.J., Laing S.M., Parsons M.E., Price C.A., Wiggall K.J.
Journal of Medicinal Chemistry , 1992
263.
A general method for the fluorine-18 labelling of fluoroquinolone antibiotics
Langer O., Mitterhauser M., Wadsak W., Brunner M., Müller U., Kletter K., Müller M.
Journal of Labelled Compounds and Radiopharmaceuticals , 2003
266.
271
Stepanov B I
Zh. Obshch. Khim. , 1962
267.
272
J. Johnston
Edin. J. Sci. (New Ser.) , 1831
269.
An Unusual Metal-Mediated Formation of an Asymmetrical Carboxylate-Bridged Dinuclear Copper(II) Complex
Keutel H., Seidel D., Klussmann M., Görls H.
Inorganic Chemistry , 2000
272.
10.1002/(SICI)1521-3773(20000204)39:3<595::AID-ANIE595>3.0.CO;2-C
274.
Asymmetric azomethine ligands based on 2-[(2-aminophenyl)aminomethylidene]-3-oxo-3-polyfluoroalkylpropionates and aldehydes
Kudyakova Y.S., Goryaeva M.V., Burgart Y.V., Saloutin V.I.
Russian Chemical Bulletin , 2010
275.
280
B. de Jassonneix
Compt. rend. , 1906
276.
Perfluoroalkylation of unsaturated compounds in the presence of copper(II) salen complexes
Kudyakova Y.S., Bazhin D.N., Burgart Y.V., Saloutin V.I., Chupakhin O.N.
Russian Journal of Organic Chemistry , 2013
277.
282
B. de Jassonneix
Compt. rend. , 1906
278.
Water-soluble 2-aminomethylidene-1,3-dicarbonyl compounds as new chalcogenide colloidal stabilizers
Bazhin D.N., Kudyakova Y.S., Gorbunova T.I., Kozhevnikova N.S., Suntsov A.Y., Burgart Y.V., Rempel’ A.A., Saloutin V.I., Chupakhin O.N.
Russian Journal of Organic Chemistry , 2013