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Preparation of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives

S A Kon'kov 1
S A Kon'kov
, 
Igor Konstantinovich Moiseev 1
Igor Konstantinovich Moiseev
, 
Margarita Nikolaevna Zemtsova 1
Margarita Nikolaevna Zemtsova
, 
K M Bormasheva 1
K M Bormasheva
1 Samara State Technical University
10.1070/RC2014v083n05ABEH004374
Published 30 November 2013
Communication , Volume 83, Issue 5, 377-390
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Kon'kov S. A. et al. Preparation of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives // Russian Chemical Reviews. 2014. Vol. 83. No. 5. pp. 377-390.
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Kon'kov S. A., Moiseev I. K., Zemtsova M. N., Bormasheva K. M. Preparation of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives // Russian Chemical Reviews. 2014. Vol. 83. No. 5. pp. 377-390.
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TY - JOUR
DO - 10.1070/RC2014v083n05ABEH004374
UR - https://rcr.colab.ws/publications/10.1070/RC2014v083n05ABEH004374
TI - Preparation of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives
T2 - Russian Chemical Reviews
AU - Kon'kov, S A
AU - Moiseev, Igor Konstantinovich
AU - Zemtsova, Margarita Nikolaevna
AU - Bormasheva, K M
PY - 2014
DA - 2013/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 377-390
IS - 5
VL - 83
ER -
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@article{2014_Kon'kov,
author = {S A Kon'kov and Igor Konstantinovich Moiseev and Margarita Nikolaevna Zemtsova and K M Bormasheva},
title = {Preparation of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives},
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/RC2014v083n05ABEH004374},
number = {5},
pages = {377--390},
doi = {10.1070/RC2014v083n05ABEH004374}
}
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Kon'kov, S. A., et al. “Preparation of heterocyclic systems based on mono- and dicarbonyl adamantane derivatives.” Russian Chemical Reviews, vol. 83, no. 5, Nov. 2014, pp. 377-390. https://rcr.colab.ws/publications/10.1070/RC2014v083n05ABEH004374.
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Abstract

Examples of the synthesis of various heterocycles containing an adamantane moiety based on mono- and dicarbonyl adamantane derivatives are considered. Systems in which the adamantane cage is spiro connected with a heterocyclic ring or is present as a part of substituent in the heterocycle are presented. Data on the biological activities of these derivatives are given.

Bibliography --- 85 references.

References

2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
The synthesis of spiro[adamantane‐[1,2]dioxetanes]
Adam W., Encarnación L.A.
Chemische Berichte , 1982
7.
Two new stereochemically complementary oxindole synthesis
Fleming I., Loreto M.A., Michael J.P., Wallace I.H.
Tetrahedron Letters , 1982
8.
New adamantane-based spiro 1,2,4-trioxanes orally effective against rodent and simian malaria.
Singh C., Kanchan R., Sharma U., Puri S.K.
Journal of Medicinal Chemistry , 2007
9.
Thio FCMA Intermediates as Strong Acyl Donors: A General Solution to the Formation of Complex Amide Bonds
Rao Y., Li X., Danishefsky S.J.
Journal of the American Chemical Society , 2009
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
Amines That Transport Protons across Bilayer Membranes:  Synthesis, Lysosomal Neutralization, and Two-Phase pKa Values by NMR
Dubowchik G.M., Padilla L., Edinger K., Firestone R.A.
Journal of Organic Chemistry , 1996
12.
Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2
Kolocouris N., Kolocouris A., Foscolos G.B., Fytas G., Neyts J., Padalko E., Balzarini J., Snoeck R., Andrei G., De Clercq E.
Journal of Medicinal Chemistry , 1996
13.
Synthesis of New 1-Adamantanecarboxylic Acid Derivatives
Dikusar1' E.A., Kozlov N.G., Potkin V.I., Yuvchenko A.P., Kovganko N.V.
Russian Journal of Organic Chemistry , 2004
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
16.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
17.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
18.
Praziquantel analogs with activity against juvenile Schistosoma mansoni.
Dong Y., Chollet J., Vargas M., Mansour N.R., Bickle Q., Alnouti Y., Huang J., Keiser J., Vennerstrom J.L.
Bioorganic and Medicinal Chemistry Letters , 2010
19.
10.1002/(SICI)1521-3897(200004)342:4<355::AID-PRAC355>3.0.CO;2-E
20.
10.1002/1521-3765(20010702)7:13<2862::AID-CHEM2862>3.0.CO;2-K
22.
Wrenchnolol Derivative Optimized for Gene Activation in Cells
Jung D., Shimogawa H., Kwon Y., Mao Q., Sato S., Kamisuki S., Kigoshi H., Uesugi M.
Journal of the American Chemical Society , 2009
23.
Discovery of benzhydrylpiperazine derivatives as CB1 receptor inverse agonists via privileged structure-based approach
Meng T., Wang J., Peng H., Fang G., Li M., Xiong B., Xie X., Zhang Y., Wang X., Shen J.
European Journal of Medicinal Chemistry , 2010
25.
Synthesis and SAR of Adatanserin:  Novel Adamantyl Aryl- and Heteroarylpiperazines with Dual Serotonin 5-HT1A and 5-HT2 Activity as Potential Anxiolytic and Antidepressant Agents
Abou-Gharbia M.A., Childers W.E., Fletcher H., McGaughey G., Patel U., Webb M.B., Yardley J., Andree T., Boast C., Kucharik R.J., Marquis K., Morris H., Scerni R., Moyer J.A.
Journal of Medicinal Chemistry , 1999
26.
Synthesis and biological activity of 1-acetyl-2,3-diaryl-1, 2,3,4-tetrahydroquinazoline-4-ones
Chernobrovin N.I., Kozhevnikov Y.V., Bobrovskaya O.V., Syropyatov B.Y.
Pharmaceutical Chemistry Journal , 1991
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
Synthesis and antiamnesic activity of a series of N-acylprolyl-containing dipeptides
Gudasheva T., Voronina T., Ostrovskaya R., Rozantsev G., Vasilevich N., Trofimov S., Kravchenko E., Skoldinov A., Seredenin S.
European Journal of Medicinal Chemistry , 1996
29.
A NOVEL C-H INSERTION VIA DEOXYGENATION OF AMIDES BY A SM/SMI2 MIXED SYSTEM
Ogawa A., Takami N., Nanke T., Ohya S., Hirao T., Sonoda N.
Tetrahedron , 1997
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
Synergism of virtual screening and medicinal chemistry: Identification and optimization of allosteric antagonists of metabotropic glutamate receptor 1
Noeske T., Trifanova D., Kauss V., Renner S., Parsons C.G., Schneider G., Weil T.
Bioorganic and Medicinal Chemistry , 2009
32.
Synthesis and hepatoprotector activity of aminoketones of the adamantane series
Kozlov N.G., Korotyshova G.P.
Pharmaceutical Chemistry Journal , 1999
33.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
36.
A stable α-lactarn derived from adamantane
Talaty E.R., Dupuy A.E., Cancienne A.E.
Journal of Heterocyclic Chemistry , 1967
37.
Synthesis and antiviral activity of adamantyloxiranes and their derivatives
Shiryaev A.K., Moiseev I.K., Boreko E.I., Korobchenko L.V., Vladyko G.V.
Pharmaceutical Chemistry Journal , 1990
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
39
V. F. Gachkovskii
Biofizika , 1959
40.
Fluorinatedβ-Diketones in Reactions with Diazocyclopropane Generated in situ
Tomilov Y., Guseva E., Kostuchenko I., Ugrak B., Shulishov E., Nefedov O.
European Journal of Organic Chemistry , 2004
41.
Simple Preparation of Diamondoid 1,3-Dienes via Oxetane Ring Opening
Fokin A.A., Butova E.D., Chernish L.V., Fokina N.A., Dahl J.E., Carlson R.M., Schreiner P.R.
Organic Letters , 2007
44.
A General Synthesis of Substituted Formylpyrroles from Ketones and 4-Formyloxazole
Reeves J.T., Song J.J., Tan Z., Lee H., Yee N.K., Senanayake C.H.
Organic Letters , 2007
45.
Thiocarbonyl S-sulfides, a new class of 1,3-dipoles
Huisgen R., Rapp J.
Journal of the American Chemical Society , 1987
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
47.
47
G. Oster
"Research in Photosynthesis" , 1957
48.
3(5)-(1-Adamantyl)pyrazoles: chemistry and molecular structure †
Claramunt R.M., López C., García M.D., Pierrot M., Giorgi M., Elguero J.
Journal of the Chemical Society Perkin Transactions 2 , 2000
49.
Antiviral Activity of Adamantane-Containing Heterocycles
Makarova N.V., Boreko E.I., Moiseev I.K., Pavlova N.I., Nikolaeva S.N., Zemtsova M.N., Vladyko G.V.
Pharmaceutical Chemistry Journal , 2002
50.
50
G. Glacomello
Gazzetta. , 1935
51.
Vilsmeier Formylation of Hydrazones and Semicarbazones Derived from Alkyl, Benzyl, and Cycloalkyl Methyl Ketones
Lebedev A.V., Lebedeva A.B., Sheludyakov V.D., Kovaleva E.A., Ustinova O.L., Kozhevnikov I.B.
Russian Journal of General Chemistry , 2005
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
53.
Synthesis of adamantyl-substituted pyrazolines
Makarova N.V., Zemtsova N.N., Moiseev I.K.
Chemistry of Heterocyclic Compounds , 1994
54.
54
R. Livingston
J. Phys. Chem. , 1941
55.
Synthesis and reactions of methyl 3-(1-adamantyl-carbonyl)-4,5-dihydro-1H-pyrazole-5-carboxylate
Lozhkin S.S., Petrov D.V., Dokichev V.A., Tomilov Y.V., Nefedov O.M.
Chemistry of Heterocyclic Compounds , 2009
56.
56
T. Iasui
Bull. Chem. Soc. Japan. , 1935
57.
Synthesis of Adamantane Derivatives. III. Synthesis of Adamantane Heterocycles
Sasaki T., Eguchi S., Toru T.
Bulletin of the Chemical Society of Japan , 1969
59.
59
H. Linshitz
"Research in Photosynthesis" , 1957
60.
Synthesis of 5-substituted 4-aminoalkylpyrazol-3-ones (isoxazol-3-ones) from 3-acyllactams
Nenajdenko V.G., Zakurdaev E.P., Gololobov A.M., Balenkova E.S.
Russian Chemical Bulletin , 2005
61.
61
A. N. Terenin
1959
62.
Metal complexes in organic synthesis—V
Gonzalez A., Marquet J., Moreno-Mañas M.
Tetrahedron , 1986
64.
Synthesis of pyrazoles and pyrazolones from 1,3- and 1,4-diketones of the adamantane series
Kon’kov S.A., Moiseev I.K.
Russian Journal of Organic Chemistry , 2009
65.
65
A. A. Krasnovskii
Biofizika , 1959
66.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
67.
Catalytic radical acetylation of adamantanes with biacetyl by a cobalt salt under atmospheric dioxygen
Kishi A., Kato S., Sakaguchi S., Ishii Y.
Chemical Communications , 1999
68.
The Activity of the New Adamantane Derivatives Against the Orthopoxviruses
Klimochkin Y., Osyanin V., Golovin E., Leonova M., Konkov S., Kilyaeva N., Bormotov N., Serova O., Balakhnin S., Belanov E.
Antiviral Research , 2010
69.
Synthesis of nitroso- and aminopyrazoles containing an adamantane fragment
Kon’kov S.A., Moiseev I.K.
Russian Journal of Organic Chemistry , 2010
70.
70
N. Bubnov
Biofizika , 1960
71.
Synthesis and Some Chemical Transformations of Adamantyl-Substituted Pyrazolones
Bormasheva K.M., Kon’kov S.A., Moiseev I.K.
Russian Journal of Organic Chemistry , 2010
72.
Reactions of adamantyl-substituted keto esters with hydrazine and phenylhydrazine
Bormasheva K.M., Nechaeva O.N., Moiseev I.K.
Russian Journal of Organic Chemistry , 2008
73.
Reaction of ethyl 3-(1-adamantyl)-3-oxopropanoate with fluorobenzoyl chlorides
Kon’kov S.A., Krylov K.S., Moiseev I.K.
Russian Journal of Organic Chemistry , 2010
74.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
75.
An infrared study of rotational isomerism in thiazole-2-carboxylates
Kaye P.T., Meakins G.D., Willbe C., Williams P.R.
Journal of the Chemical Society Perkin Transactions 1 , 1981
76.
4-(1-Adamantyl)-1,2,3-thiadiazole as a source of adamantylethynyl sulfides
Petrov M.L., Shchipalkin A.A., Kuznetsov V.A.
Russian Journal of Organic Chemistry , 2007
77.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
78.
New synthesis of 4-(1-adamantyl)-2-aryl-1,3-thiazoles from 4-(1-adamantyl)-1,2,3-thiadiazole
Shchipalkin A.A., Petrov M.L., Kuznetsov V.A.
Russian Journal of Organic Chemistry , 2011
79.
82
G. P. Brin
Biokhimiya , 1957
80.
Nickel-Catalyzed Olefination of Unactivated Aliphatic Dithioacetals
Huang L., Huang C., Stulgies B., de Meijere A., Luh T.
Organic Letters , 2003
81.
Synthesis and Cyclization of Diketones from the Adamantane Series
Makarova N.V., Moiseev I.K., Zemtsova M.N.
Russian Journal of Organic Chemistry , 2001
82.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
84.
Reactions of indoles with 2- and 4-hydroxybenzyl alcohols
Osyanin V.A., Sidorina N.E., Klimochkin Y.N.
Russian Journal of General Chemistry , 2011
85.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
86.
Syntheses based on bromomethyl 1-adamantyl ketone
Makaraova N.V., Zemtsova M.N., Moiseev I.K.
Chemistry of Heterocyclic Compounds , 1993
87.
90
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1951
89.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
90.
Novel Potent and Selective Central 5-HT3 Receptor Ligands Provided with Different Intrinsic Efficacy. 1. Mapping the Central 5-HT3 Receptor Binding Site by Arylpiperazine Derivatives
Cappelli A., Anzini M., Vomero S., Mennuni L., Makovec F., Doucet E., Hamon M., Bruni G., Romeo M.R., Menziani M.C., De Benedetti P.G., Langer T.
Journal of Medicinal Chemistry , 1998
91.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
94.
Novel Potent and Selective Central 5-HT3 Receptor Ligands Provided with Different Intrinsic Efficacy. 2. Molecular Basis of the Intrinsic Efficacy of Arylpiperazine Derivatives at the Central 5-HT3 Receptors
Cappelli A., Anzini M., Vomero S., Canullo L., Mennuni L., Makovec F., Doucet E., Hamon M., Menziani M.C., De Benedetti P.G., Bruni G., Romeo M.R., Giorgi G., Donati A.
Journal of Medicinal Chemistry , 1999
96.
The o-Amino-Trifluoromethyl Functionality as a Novel Synthon for 4-Fluoroquinolines
Strekowski L., Kiselyov A.S., Hojjat M.
Journal of Organic Chemistry , 1994
97.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
98.
Synthesis and antimicrobial activity of 4-substituted 2-cycloalkylquinolines
Moiseev I.K., Zemtsova M.N., Trakhtenberg P.L., Kulikova D.A., Skobkina I.P., Neshchadim G.N., Ostapchuk N.V.
Pharmaceutical Chemistry Journal , 1988
99.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
100.
Heterocyclic Ortho-Aminocarbonyl Compounds in the Friedländer Reaction Promoted by Chlorotrimethylsilane
V. Ryabukhin S., S. Plaskon A., S. Naumchik V., M. Volochnyuk D., E. Pipko S., A. Tolmachev A.
Heterocycles , 2007
101.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
102.
Optimization of 1,3,4-Benzotriazepine-Based CCK2 Antagonists to Obtain Potent, Orally Active Inhibitors of Gastrin-Mediated Gastric Acid Secretion
McDonald I.M., Black J.W., Buck I.M., Dunstone D.J., Griffin E.P., Harper E.A., Hull R.A., Kalindjian S.B., Lilley E.J., Linney I.D., Pether M.J., Roberts S.P., Shaxted M.E., Spencer J., Steel K.I., et. al.
Journal of Medicinal Chemistry , 2007