Home / Articles / A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction

A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction

Natal'ya Aleksandrovna Danilkina 1
Natal'ya Aleksandrovna Danilkina
, 
Anna Andreevna Vasileva 1
Anna Andreevna Vasileva
, 
Irina Anatol'evna Balova 1
Irina Anatol'evna Balova
1 Saint Petersburg State University
10.1070/RCR4902
Published 30 November 2019
Review , RCR4902, Volume 89, Issue 1, 125-171
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Danilkina N. A., Vasileva A. A., Balova I. A. A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction // Russian Chemical Reviews. 2019. Vol. 89. No. 1. pp. 125-171.
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Danilkina N. A., Vasileva A. A., Balova I. A. A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction // Russian Chemical Reviews. 2019. Vol. 89. No. 1. pp. 125-171.
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TY - JOUR
DO - 10.1070/RCR4902
UR - https://rcr.colab.ws/publications/10.1070/RCR4902
TI - A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction
T2 - Russian Chemical Reviews
AU - Danilkina, Natal'ya Aleksandrovna
AU - Vasileva, Anna Andreevna
AU - Balova, Irina Anatol'evna
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 125-171
IS - 1
VL - 89
ER -
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@article{2019_Danilkina,
author = {Natal'ya Aleksandrovna Danilkina and Anna Andreevna Vasileva and Irina Anatol'evna Balova},
title = {A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4902},
number = {1},
pages = {125--171},
doi = {10.1070/RCR4902}
}
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Danilkina, Natal'ya Aleksandrovna, et al. “A.E. Favorskii's scientific legacy in modern organic chemistry: prototropic acetyleneallene isomerization and the acetylene zipper reaction.” Russian Chemical Reviews, vol. 89, no. 1, Nov. 2019, pp. 125-171. https://rcr.colab.ws/publications/10.1070/RCR4902.
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Keywords

"acetylene zipper"
acetylene-allene isomerization
diacetylenes
Favorskii reaction
Favorskii rearrangement
metylacetylenes
propargyl alcohols
retro-Favorskii reaction
terminal acetylens

Abstract

Alexei Evgrafovich Favorskii was an outstanding organic chemist who left a great scientific legacy as a result of long time and fruitful work. Most of the theoretically and practically important discoveries of A.E.Favorskii were made in the chemistry of acetylene and its derivatives. Nowadays, the reactions discovered by him, which include acetylene--allene isomerization, the Favorskii and retro-Favorskii reactions, the Favorskii rearrangement and the vinylation reaction, are widely used in industry and in laboratory synthesis. This review summarizes the main scientific achievements of A.E.Favorskii, as well as their development in modern organic chemistry. Much consideration is given to acetylene--allene isomerization as a convenient method for the synthesis of methyl-substituted acetylenes and to the acetylene zipper reaction as a synthetic tool for obtaining terminal acetylenes. The review presents examples of the application of these reactions in modern organic synthesis of complex molecules, including natural compounds and their analogues.

The bibliography includes 266 references.

Funders

Russian Foundation for Basic Research
18-33-01265 мол_а

References

1.
rcr_89_1_125bib1
Favorskaya
1980
2.
rcr_89_1_125bib2
Favorskaya
2019
3.
Modern Trends of Organic Chemistry in Russian Universities
Konovalov A.I., Antipin I.S., Burilov V.A., Madzhidov T.I., Kurbangalieva A.R., Nemtarev A.V., Solovieva S.E., Stoikov I.I., Mamedov V.A., Zakharova L.Y., Gavrilova E.L., Sinyashin O.G., Balova I.A., Vasilyev A.V., Zenkevich I.G., et. al.
Russian Journal of Organic Chemistry , 2018
4.
[3 + 2]-Cycloaddition reaction of sydnones with alkynes
Hladíková V., Váňa J., Hanusek J.
Beilstein Journal of Organic Chemistry , 2018
5.
1,3-Dipolar cycloaddition reactions of azomethine ylides and alkynes
Gulevskaya A.V., Nelina-Nemtseva J.I.
Chemistry of Heterocyclic Compounds , 2018
6.
Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)
Svete J., Grošelj U., Požgan F., Štefane B.
Synthesis , 2018
7.
Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends
Wang C., Ikhlef D., Kahlal S., Saillard J., Astruc D.
Coordination Chemistry Reviews , 2016
8.
Acetylene–azide click macrocyclization of peptides
Zakharova E.A., Shmatova O.I., Nenajdenko V.G.
Russian Chemical Reviews , 2018
9.
Transition metal catalyzed element–element′ additions to alkynes
Ansell M.B., Navarro O., Spencer J.
Coordination Chemistry Reviews , 2017
10.
Hydrostannation of Alkynes
Alami M., Hamze A., Provot O.
ACS Catalysis , 2019
12.
Advances in chemoselective and/or stereoselective semihydrogenation of alkynes
Swamy K.C., Reddy A.S., Sandeep K., Kalyani A.
Tetrahedron Letters , 2018
14.
Recent Advances in the Addition of Amide/Sulfonamide Bonds to Alkynes
Zhao F., Li P., Liu X., Jia X., Wang J., Liu H.
Molecules , 2019
16.
Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry
Alabugin I., Gonzalez-Rodriguez E., Kawade R., Stepanov A., Vasilevsky S.
Molecules , 2019
17.
rcr_89_1_125bib17
Huang
Chem. Commun. , 2018
18.
Acetylene in Organic Synthesis: Recent Progress and New Uses
Voronin V.V., Ledovskaya M.S., Bogachenkov A.S., Rodygin K.S., Ananikov V.P.
Molecules , 2018
20.
Alkynes as Privileged Synthons in Selected Organic Name Reactions.
Heravi M.M., Dehghani M., Zadsirjan V., Ghanbarian M.
Current Organic Synthesis , 2019
21.
Catalytic reactions of acetylene: a feedstock for the chemical industry revisited.
Trotuş I., Zimmermann T., Schüth F.
Chemical Reviews , 2013
22.
rcr_89_1_125bib22
Favorskii
Zh. Rus. Fiz.-Khim. O-va , 1892
23.
rcr_89_1_125bib23
Men’shutkin
Zh. Rus. Fiz.-Khim. O-va , 1901
24.
Recent applications of the 1,2-carbon atom migration strategy in complex natural product total synthesis.
Zhang X., Tu Y., Zhang F., Chen Z., Wang S.
Chemical Society Reviews , 2017
25.
rcr_89_1_125bib25
Siengalewicz
2014
26.
rcr_89_1_125bib26
Butkus
2014
27.
The Favorskii Rearrangement: Synthetic Applications
Guijarro D., Yus M.
Current Organic Chemistry , 2005
28.
rcr_89_1_125bib28
Harmata
2015
33.
Total Synthesis of Entecavir: A Robust Route for Pilot Production
Xu H., Wang F., Xue W., Zheng Y., Wang Q., Qiu F.G., Jin Y.
Organic Process Research and Development , 2018
35.
Favorskii-Type Rearrangement of the 4,5-Epoxymorphinan Skeleton.
Kutsumura N., Koyama Y., Suzuki Y., Tominaga K., Yamamoto N., Saitoh T., Nagumo Y., Nagase H.
Organic Letters , 2018
36.
4-Hydroxyphenacyl Ammonium Salts: A Photoremovable Protecting Group for Amines in Aqueous Solutions.
Bownik I., Šebej P., Literák J., Heger D., Šimek Z., Givens R.S., Klán P.
Journal of Organic Chemistry , 2015
38.
rcr_89_1_125bib38
Favorskii
Zh. Rus. Fiz.-Khim. O-va , 1900
39.
Reppe W., Mitarbeitern
1955
40.
rcr_89_1_125bib40
Pässler
2011
41.
rcr_89_1_125bib41
42.
rcr_89_1_125bib42
44.
The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups
Trost B., Weiss A.
Advanced Synthesis and Catalysis , 2009
45.
Reactions of acetylenes in superbasic media. Recent advances
Trofimov B.A., Schmidt E.Y.
Russian Chemical Reviews , 2014
46.
Trofimov Boris Aleksandrovich, Schmidt Elena Yur'evna, Bidusenko Ivan A., Cherimichkina Natalia Aleksandrovna
Mendeleev Communications , 2014
47.
A convenient synthesis of hetarylethynyl ketones from hetarylcarbaldehydes and acetylene
Tomilin D.N., Petrova O.V., Sobenina L.N., Mikhaleva A.I., Trofimov B.A.
Chemistry of Heterocyclic Compounds , 2013
48.
First example of favorskii ethynylation of pyrrolecarbaldehydes: Synthesis of 1-(1-methyl-1H-pyrrol-2-yl)prop-2-yn-1-ol
Sobenina L.N., Petrova O.V., Tomilin D.N., Ivanov A.V., Shcherbakova V.S., Mikhaleva A.I., Trofimov B.A.
Russian Journal of Organic Chemistry , 2015
49.
Improved synthesis of tertiary propargyl alcohols by the Favorskii reaction of alkyl aryl (hetaryl) ketones with acetylene
Shmidt E.Y., Bidusenko I.A., Protsuk N.I., Mikhaleva A.I., Trofimov B.A.
Russian Journal of Organic Chemistry , 2013
50.
2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
Ivanov A.V., Shcherbakova V.S., Ushakov I.A., Sobenina L.N., Petrova O.V., Mikhaleva A.I., Trofimov B.A.
Beilstein Journal of Organic Chemistry , 2015
51.
First Example of the Aza-Favorskii Reaction. Ethynylation of C=N Bond in the Superbasic System t-BuOK–DMSO
Bidusenko I.A., Schmidt E.Y., Trofimov B.A.
Russian Journal of Organic Chemistry , 2018
52.
Mirsakiyeva A., Botkina D., Elgammal K., Ten A., Hugosson H.W., Delin A., Yu V.
Arkivoc , 2016
53.
2‐Propargyl Alcohols in Organic Synthesis
Qian H., Huang D., Bi Y., Yan G.
Advanced Synthesis and Catalysis , 2019
55.
Recent advances in Sonogashira reactions
Chinchilla R., Nájera C.
Chemical Society Reviews , 2011
56.
rcr_89_1_125bib56
Chodkiewicz
Hebd. Seances Acad. Sci. , 1955
59.
rcr_89_1_125bib59
Wu
New J. Chem. , 2018
60.
rcr_89_1_125bib60
Baranov
2018
66.
Palladium-Catalyzed One-Pot Consecutive Amination and Sonogashira Coupling for Selective Synthesis of 2-Alkynylanilines
Pan S., Ma X., Zhong D., Chen W., Liu M., Wu H.
Advanced Synthesis and Catalysis , 2015
67.
rcr_89_1_125bib67
Andrade
2019
69.
rcr_89_1_125bib69
West
2008
70.
1-Iodobuta-1,3-diynes in Copper-Catalyzed Azide–Alkyne Cycloaddition: A One-Step Route to 4-Ethynyl-5-iodo-1,2,3-triazoles
Govdi A.I., Danilkina N.A., Ponomarev A.V., Balova I.A.
Journal of Organic Chemistry , 2019
71.
Synthesis of Terminal Ethynyl Aryl Selenides and Sulfides Based on the Retro-Favorskii Reaction of Hydroxypropargyl Precursors.
Lopes E.F., Dalberto B.T., Perin G., Alves D., Barcellos T., Lenardão E.J.
Chemistry - A European Journal , 2017
72.
rcr_89_1_125bib72
Favorskii
Zh. Rus. Fiz.-Khim. O-va , 1888
73.
Methods for the synthesis of O-, S- and N-vinyl derivatives
Ledovskaya M.S., Voronin V.V., Rodygin K.S.
Russian Chemical Reviews , 2018
75.
rcr_89_1_125bib75
L’vov
Zh. Rus. Fiz.-Khim. O-va , 1884
76.
rcr_89_1_125bib76
Favorskii
Zh. Rus. Fiz.-Khim. O-va , 1886
77.
rcr_89_1_125bib77
Musabekov
1958
79.
Base-catalysed isomerisation of acetylenes
Bushby R.J.
Quarterly Reviews Chemical Society , 1970
80.
rcr_89_1_125bib80
Theron
1978
81.
rcr_89_1_125bib81
Pines
1977
82.
rcr_89_1_125bib82
Smadja
Compt. rend. , 1964
83.
rcr_89_1_125bib83
Avocetien
2014
85.
Propargyloxy- and allenyloxymethylferrocenes: Synthesis and oligomerization
Tarasova O.A., Tatarinova I.V., Vakul'skaya T.I., Khutsishvili S.S., Smirnov V.I., Klyba L.V., Prozorova G.F., Mikhaleva A.I., Trofimov B.A.
Journal of Organometallic Chemistry , 2013
87.
Expeditious synthesis of 9-allenylpurines via cesium carbonate catalyzed isomerization of 9-alkynylpurines
Yu M., Liu X., Jiang Q., Du H.
Phosphorus, Sulfur and Silicon and the Related Elements , 2018
88.
Assessment of reagents for selenocysteine conjugation and the stability of selenocysteine adducts.
Pedzisa L., Li X., Rader C., Roush W.R.
Organic and Biomolecular Chemistry , 2016
90.
Acetylene: new prospects of classical reactions
Trofimov B.A., Gusarova N.K.
Russian Chemical Reviews , 2007
91.
rcr_89_1_125bib91
Reissig
2014
92.
PPh3AuTFA Catalyzed in the Dearomatization of 2-Naphthols with Allenamides.
An J., Lombardi L., Grilli S., Bandini M.
Organic Letters , 2018
93.
Palladium/Copper Co-Catalyzed Cascade Metallo-ene/Sonogashira Coupling Reaction of Allenamides
Liang H., Meng L., Chi X., Yao S., Chen H., Jiao L., Liu Q., Zhang D., Liu H., Dong Y.
Asian Journal of Organic Chemistry , 2018
95.
rcr_89_1_125bib95
Richter
2018
96.
rcr_89_1_125bib96
Nedolya
2018
97.
rcr_89_1_125bib97
Yang
2018
100.
DBU-Catalyzed Alkyne-Imidate Cyclization toward 1-Alkoxypyrazino[1,2- a]indole Synthesis.
Festa A.A., Zalte R.R., Golantsov N.E., Varlamov A.V., Van der Eycken E.V., Voskressensky L.G.
Journal of Organic Chemistry , 2018
101.
rcr_89_1_125bib101
Li
New J. Chem. , 2018
102.
Palladium-catalyzed intermolecular [4 + 2] formal cycloaddition with (Z)-3-iodo allylic nucleophiles and allenamides.
Yan F., Liang H., Ai B., Liang W., Jiao L., Yao S., Zhao P., Liu Q., Dong Y., Liu H.
Organic and Biomolecular Chemistry , 2019
104.
rcr_89_1_125bib104
Favorskii
Zh. Rus. Fiz.-Khim. O-va , 1887
105.
Rearrangements Involving 1-Pentyne, 2-Pentyne and 1,2-Pentadiene1
Jacobs T.L., Akawie R., Cooper R.G.
Journal of the American Chemical Society , 1951
106.
Base-Catalyzed Intramolecular 1,3- and 1,5-Proton Transfers
Cram D.J., Willey F., Fischer H.P., Scott D.A.
Journal of the American Chemical Society , 1964
107.
Acetylene–allene isomerisations. Part I. Base catalysis by potassium t-butoxide in t-butyl alcohol
Carr M.D., Gan L.H., Reid I.
Journal of the Chemical Society Perkin Transactions 2 , 1973
109.
rcr_89_1_125bib109
Julia
1964
110.
rcr_89_1_125bib110
AMostamandi
Zh. Org. Khim. , 1981
111.
rcr_89_1_125bib111
Remizova
Zh. Org. Khim. , 1980
115.
Deuteration of cycloalkynes
Abrams S., Shaw A.
Tetrahedron Letters , 1985
116.
Mechanism of the base-catalyzed prototropic propargylic rearrangement in vicinal diamines
Wotiz J.H., Barelski P.M., Koster D.F.
Journal of Organic Chemistry , 1973
118.
On the mechanism of 1,3-prototropic shifts in acetylene-allene isomerizations
Abrams S.R., Shaw A.C.
Journal of Organic Chemistry , 1987
119.
Stereogenic Propargylic Centers via Base-Mediated Terminal Allene Isomerization.
Spence J.D., Wyatt J.K., Bender D.M., Moss D.K., Nantz M.H.
Journal of Organic Chemistry , 1996
121.
The influence of distal substitution on the base-induced isomerization of long-chain terminal alkynes
Mohammad I., Mun J., Onorato A., Morton M.D., Saleh A.I., Smith M.B.
Tetrahedron Letters , 2017
124.
Organomagnesium-catalyzed isomerization of terminal alkynes to allenes and internal alkynes.
Rochat R., Yamamoto K., Lopez M.J., Nagae H., Tsurugi H., Mashima K.
Chemistry - A European Journal , 2015
125.
Soft Propargylic Deprotonation: Designed Ligand Enables Au-Catalyzed Isomerization of Alkynes to 1,3-Dienes
Wang Z., Wang Y., Zhang L.
Journal of the American Chemical Society , 2014
126.
Alkali Metal-Hydroxide-Catalyzed C(sp)-H Bond silylation.
Toutov A.A., Betz K.N., Schuman D.P., Liu W., Fedorov A., Stoltz B.M., Grubbs R.H.
Journal of the American Chemical Society , 2017
127.
Development of an Alkyne Analogue of the de Mayo Reaction: Synthesis of Medium-Sized Carbacycles and Cyclohepta[b]indoles.
Tymann D., Tymann D.C., Bednarzick U., Iovkova‐Berends L., Rehbein J., Hiersemann M.
Angewandte Chemie - International Edition , 2018
128.
Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates.
Ponath S., Menger M., Grothues L., Weber M., Lentz D., Strohmann C., Christmann M.
Angewandte Chemie - International Edition , 2018
129.
Alkaline Earth Catalysis of Alkynyl Alcohol Hydroalkoxylation/Cyclization
Brinkmann C., Barrett A.G., Hill M.S., Procopiou P.A., Reid S.
Organometallics , 2012
130.
Identification and synthesis of macrolide pheromones of the grain beetle Oryzaephilus surinamensis and the frog Spinomantis aglavei.
Hötling S., Haberlag B., Tamm M., Collatz J., Mack P., Steidle J.L., Vences M., Schulz S.
Chemistry - A European Journal , 2014
131.
Polyunsaturated alkyl amides from Echinacea: synthesis of diynes, enynes, and dienes.
Matovic N.J., Hayes P.Y., Penman K., Lehmann R.P., De Voss J.J.
Journal of Organic Chemistry , 2011
133.
Tandem Rh-catalysis: decarboxylative β-keto acid and alkyne cross-coupling.
Cruz F.A., Chen Z., Kurtoic S.I., Dong V.M.
Chemical Communications , 2016
135.
Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of signalling.
Kadirvel M., Fanimarvasti F., Forbes S., McBain A., Gardiner J.M., Brown G.D., Freeman S.
Chemical Communications , 2014
136.
rcr_89_1_125bib136
Li
J. Am. Chem. Soc. , 2012
138.
rcr_89_1_125bib138
Farcet
2013
139.
Catalytic metathesis of conjugated diynes.
Lysenko S., Volbeda J., Jones P.G., Tamm M.
Angewandte Chemie - International Edition , 2012
140.
Cyclopropenones for Metabolic Targeting and Sequential Bioorthogonal Labeling.
Row R.D., Shih H., Alexander A.T., Mehl R.A., Prescher J.A.
Journal of the American Chemical Society , 2017
142.
Gold(I)‐Catalysed Cyclisation of Alkynoic Acids: Towards an Efficient and Eco‐Friendly Synthesis of γ‐, δ‐ and ϵ‐Lactones
Gasperini D., Maggi L., Dupuy S., Veenboer R.M., Cordes D.B., Slawin A.M., Nolan S.P.
Advanced Synthesis and Catalysis , 2016
144.
Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
Ma C., Letort A., Aouzal R., Wilkes A., Maiti G., Farrugia L.J., Ricard L., Prunet J.
Chemistry - A European Journal , 2016
145.
Highly efficient synthesis of the tricyclic core of Taxol by cascade metathesis.
Letort A., Aouzal R., Ma C., Long D., Prunet J.
Organic Letters , 2014
147.
Ligand and substrate effects during Pd-catalyzed cyclizations of alkyne-tethered cyclohexadienones.
Tello-Aburto R., Kalstabakken K.A., Harned A.M.
Organic and Biomolecular Chemistry , 2013
148.
A practical and scaleable total synthesis of the jaborandi alkaloid (+)-pilocarpine
Davies S.G., Roberts P.M., Stephenson P.T., Storr H.R., Thomson J.E.
Tetrahedron , 2009
149.
Syntheses of the racemic jaborandi alkaloids pilocarpine, isopilocarpine and pilosinine
Davies S.G., Roberts P.M., Stephenson P.T., Thomson J.E.
Tetrahedron Letters , 2009
150.
Nonracemic synthesis of GK-GKRP disruptor AMG-3969.
Bourbeau M.P., Ashton K.S., Yan J., St. Jean D.J.
Journal of Organic Chemistry , 2014
151.
Small molecule disruptors of the glucokinase-glucokinase regulatory protein interaction: 3. Structure-activity relationships within the aryl carbinol region of the N-arylsulfonamido-N'-arylpiperazine series.
Nishimura N., Norman M.H., Liu L., Yang K.C., Ashton K.S., Bartberger M.D., Chmait S., Chen J., Cupples R., Fotsch C., Helmering J., Jordan S.R., Kunz R.K., Pennington L.D., Poon S.F., et. al.
Journal of Medicinal Chemistry , 2014
152.
A Novel One‐Pot, Two‐Step Synthesis of Polycyclic Indoles via Tandem Intramolecular Hydroamidation/Palladium‐Catalyzed Annulation
Liu J., Zhang Y., Li G., Roschangar F., Farina V., Senanayake C.H., Lu B.Z.
Advanced Synthesis and Catalysis , 2010
155.
rcr_89_1_125bib155
Enkelmann
1984
156.
Alekseev Alexander Sergeevich, Domnin Ivan Nikitovich, Ivanov Artem B, Arkharova Natalya Andreevna, Klechkovskaya Vera Vsevolodovna
Mendeleev Communications , 2018
157.
Alekseev Alexander Sergeevich, Domnin Ivan Nikitovich, Ivanov Artem B, Tereschenko Nadezhda Alekseevna
Mendeleev Communications , 2018
158.
The red, purple and blue modifications of polymeric unsymmetrical hydroxyalkadiynyl-N-arylcarbamate derivatives in Langmuir-Schaefer films
Alekseev A., Ihalainen P., Ivanov A., Domnin I., Klechkovskaya V., Orekhov A., Lemmetyinen H., Vuorimaa-Laukkanen E., Peltonen J., Vyaz'min S.
Thin Solid Films , 2016
159.
Stable blue phase polymeric Langmuir-Schaefer films based on unsymmetrical hydroxyalkadiynyl N-arylcarbamate derivatives
Alekseev A., Ihalainen P., Ivanov A., Domnin I., Rosqvist E., Lemmetyinen H., Vuorimaa-Laukkanen E., Peltonen J., Vyaz'min S.
Thin Solid Films , 2018
160.
Self-Assembly and Solid-State Polymerization of Butadiyne Derivatives with Amide and Trialkoxyphenyl Groups
Kikuchi K., Tatewaki Y., Okada S.
Bulletin of the Chemical Society of Japan , 2017
164.
rcr_89_1_125bib164
Nickel
Chem. – Eur. J. , 2015
165.
Design and synthesis of silicon-containing fatty acid amide derivatives as novel peroxisome proliferator-activated receptor (PPAR) agonists.
Kajita D., Nakamura M., Matsumoto Y., Ishikawa M., Hashimoto Y., Fujii S.
Bioorganic and Medicinal Chemistry Letters , 2015
166.
Discovery of a Fluorinated Enigmol Analog with Enhanced in Vivo Pharmacokinetic and Anti-Tumor Properties.
Miller E.J., Mays S.G., Baillie M.T., Howard R.B., Culver D.G., Saindane M., Pruett S.T., Holt J.J., Menaldino D.S., Evers T.J., Reddy G.P., Arrendale R.F., Natchus M.G., Petros J.A., Liotta D.C., et. al.
ACS Medicinal Chemistry Letters , 2016
167.
Synthesis and activity of polyacetylene substituted 2-hydroxy acids, esters, and amides against microbes of clinical importance.
Kyi S., Wongkattiya N., Warden A.C., O’Shea M.S., Deighton M., Macreadie I., Graichen F.H.
Bioorganic and Medicinal Chemistry Letters , 2010
170.
Identification of a novel NAMPT inhibitor by combinatorial click chemistry and chemical refinement
Theeramunkong S., Galli U., Grolla A.A., Caldarelli A., Travelli C., Massarotti A., Troiani M.P., Alisi M.A., Orsomando G., Genazzani A.A., Tron G.C.
MedChemComm , 2015
171.
Comparing the reactivity of alkynes and alkenes on silicon (100) surfaces.
Ng A., Ciampi S., James M., Harper J.B., Gooding J.J.
Langmuir , 2009
172.
rcr_89_1_125bib172
Polyakova
2009
173.
6,6'-Dimethyl-2,2'-bipyridine-4-ester: A pivotal synthon for building tethered bipyridine ligands
Havas F., Leygue N., Danel M., Mestre B., Galaup C., Picard C.
Tetrahedron , 2009
174.
Inhibition of Acinetobacter baumannii biofilm formation on a methacrylate polymer containing a 2-aminoimidazole subunit.
Peng L., DeSousa J., Su Z., Novak B.M., Nevzorov A.A., Garland E.R., Melander C.
Chemical Communications , 2011
175.
Synthesis and biological activity of 2-aminoimidazole triazoles accessed by Suzuki-Miyaura cross-coupling.
Reyes S., Huigens III R.W., Su Z., Simon M.L., Melander C.
Organic and Biomolecular Chemistry , 2011
176.
rcr_89_1_125bib176
Dey
Chem. – Eur. J. , 2017
178.
Pd(0)-catalyzed alkene oxy- and aminoalkynylation with aliphatic bromoacetylenes.
Nicolai S., Sedigh-Zadeh R., Waser J.
Journal of Organic Chemistry , 2013
179.
Fused ring aziridines as a facile entry into triazole fused tricyclic and bicyclic heterocycles.
Fang F., Vogel M., Hines J.V., Bergmeier S.C.
Organic and Biomolecular Chemistry , 2012
181.
Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives.
Kobayashi Y., Morita M., Ogawa N., Kondo D., Tojo T.
Organic and Biomolecular Chemistry , 2016
182.
Phase separation as a strategy toward controlling dilution effects in macrocyclic Glaser-Hay couplings.
Bédard A., Collins S.K.
Journal of the American Chemical Society , 2011
184.
Cu(I)-catalyzed macrocyclic Sonogashira-type cross-coupling.
Santandrea J., Bédard A., Collins S.K.
Organic Letters , 2014
185.
rcr_89_1_125bib185
Rangaraju
2018
186.
Tetris in monolayers: patterned self-assembly using side chain shape.
Xue Y., Zimmt M.B.
Chemical Communications , 2011
188.
rcr_89_1_125bib188
Yang
Langmuir , 2015
190.
Identification of Novel Triazole-Based Nicotinamide Phosphoribosyltransferase (NAMPT) Inhibitors Endowed with Antiproliferative and Antiinflammatory Activity.
Travelli C., Aprile S., Rahimian R., Grolla A.A., Rogati F., Bertolotti M., Malagnino F., di Paola R., Impellizzeri D., Fusco R., Mercalli V., Massarotti A., Stortini G., Terrazzino S., Del Grosso E., et. al.
Journal of Medicinal Chemistry , 2017
191.
rcr_89_1_125bib191
Shibakami
2009
192.
Total synthesis of clathculins A and B.
Hoye R.C., Anderson G.L., Brown S.G., Schultz E.E.
Journal of Organic Chemistry , 2010
193.
Site‐specific 2H‐labeled oleic acid and derived esters for use as tracers of ethyl oleate metabolism in honey bees
Chen H., Plettner E.
Journal of Labelled Compounds and Radiopharmaceuticals , 2011
194.
Penta‐deuterated acid precursors in the pheromone biosynthesis of the Egyptian armyworm, Spodoptera littoralis
Muñoz L., Rosell G., Guerrero A.
Journal of Labelled Compounds and Radiopharmaceuticals , 2009
196.
Synthesis of natural polyacetylenes bearing furan rings.
Barancelli D.A., Mantovani A.C., Jesse C., Nogueira C.W., Zeni G.
Journal of Natural Products , 2009
197.
Total synthesis of the triglycosyl phenolic glycolipid PGL-tb1 from Mycobacterium tuberculosis.
Barroso S., Castelli R., Baggelaar M.P., Geerdink D., ter Horst B., Casas-Arce E., Overkleeft H.S., van der Marel G.A., Codée J.D., Minnaard A.J.
Angewandte Chemie - International Edition , 2012
200.
Capture and Release of Alkyne-Derivatized Glycerophospholipids Using Cobalt Chemistry
Milne S.B., Tallman K.A., Serwa R., Rouzer C.A., Armstrong M.D., Marnett L.J., Lukehart C.M., Porter N.A., Brown H.A.
Nature Chemical Biology , 2010
201.
2-Bromopalmitate analogues as activity-based probes to explore palmitoyl acyltransferases.
Zheng B., DeRan M., Li X., Liao X., Fukata M., Wu X.
Journal of the American Chemical Society , 2013
202.
Mono-fluorinated alkyne-derived SAMs on oxide-free Si(111) surfaces: preparation, characterization and tuning of the Si workfunction.
Pujari S.P., van Andel E., Yaffe O., Cahen D., Weidner T., van Rijn C.J., Zuilhof H.
Langmuir , 2013
203.
Syntheses of photoreactive cardiolipins for a photoaffinity labeling study
Abe M., Nakano M., Kosaka A., Miyoshi H.
Tetrahedron Letters , 2015
207.
A carbohydrate approach for the formal total synthesis of (−)-aspergillide C
Srihari P., Hari Krishna N., Sridhar Y., Kamal A.
Beilstein Journal of Organic Chemistry , 2014
210.
rcr_89_1_125bib210
Xing
2009
211.
An efficient total synthesis of (+)-Cladospolide C
Raji Reddy C., Narsimha Rao N.
Tetrahedron Letters , 2009
212.
rcr_89_1_125bib212
Raji Reddy
2012
213.
rcr_89_1_125bib213
Chinnababu
2012
214.
rcr_89_1_125bib214
Rao
2018
215.
Long-range shielding effects in the (1)H NMR spectra of Mosher-like ester derivatives.
Hoye T.R., Erickson S.E., Erickson-Birkedahl S.L., Hale C.R., Izgu E.C., Mayer M.J., Notz P.K., Renner M.K.
Organic Letters , 2010
216.
Divergent total synthesis of penaresidin B and its straight side chain analogue
Fujiwara T., Hashimoto K., Umeda M., Murayama S., Ohno Y., Liu B., Nambu H., Yakura T.
Tetrahedron , 2018
217.
Versatile Synthesis of the C3−C14 Domain of 7-Deoxyokadaic Acid
Trygstad T.M., Pang Y., Forsyth C.J.
Journal of Organic Chemistry , 2008
218.
Asymmetric total synthesis of soraphen A: a flexible alkyne strategy.
Trost B., Sieber J., Qian W., Dhawan R., Ball Z.
Angewandte Chemie - International Edition , 2009
220.
Intramolecular hydroamination of conjugated enynes
Zhang W., Werness J.B., Tang W.
Tetrahedron , 2009
221.
rcr_89_1_125bib221
Remizova
Zh. Org. Khim. , 1986
222.
rcr_89_1_125bib222
Balova
Russ. J. Org. Chem. , 1991
223.
rcr_89_1_125bib223
Balova
Russ. J. Org. Chem. , 2000
224.
Convenient synthesis of dodeca-1,3-diynyl ketones by the “diacetylene zipper” reaction
Novikov R.V., Vasil'ev A.A., Balova I.A.
Russian Chemical Bulletin , 2005
225.
“Acetylene Zipper” Reactions and Pd-Cu-Catalyzed Cross-coupling in the Synthesis of Vicinal 1,3-Alkadiynylarylamines and Aminopyridines
Balova I.A., Morozkina S.N., Sorokoumov V.N., Vinogradova O.V., Vasilevskii S.F.
Russian Journal of Organic Chemistry , 2003
226.
rcr_89_1_125bib226
Balova
2005
227.
Sorokoumov Victor Nikolaevich, Popik Vladimir V, Balova Irina Anatol'evna
Mendeleev Communications , 2011
228.
rcr_89_1_125bib228
Balova
Russ. J. Org. Chem. , 1993
229.
Synthesis and properties of diacetylene azides
Domnin I.N., Remizova L.A.
Russian Journal of Organic Chemistry , 2009
230.
An acetylene zipper—Sonogashira reaction sequence for the efficient synthesis of conjugated arylalkadiynols
Kulyashova A.E., Sorokoumov V.N., Popik V.V., Balova I.A.
Tetrahedron Letters , 2013
232.
Intramolecular cyclizations of functionalized diynes
Danilkina N.A., Kulyashova A.E., Balova I.A.
Chemistry of Heterocyclic Compounds , 2012
233.
The Richter reaction of ortho-(alka-1,3-diynyl)aryldiazonium salts
Vinogradova O.V., Sorokoumov V.N., Vasilevsky S.F., Balova I.A.
Tetrahedron Letters , 2007
235.
Study of cyclyzation of o-(1-Alkynyl)- and o-(1,3-Butadiynyl)aryltriazenes under the action of acids
Danilkina N.A., Gorbunova E.G., Sorokoumov V.N., Balova I.A.
Russian Journal of Organic Chemistry , 2012
236.
Electrophilic Cyclization of Aryldiacetylenes in the Synthesis of Functionalized Enediynes Fused to a Heterocyclic Core
Danilkina N.A., Kulyashova A.E., Khlebnikov A.F., Bräse S., Balova I.A.
Journal of Organic Chemistry , 2014
237.
rcr_89_1_125bib237
Danilkina
2012
238.
Beyond copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition: Synthesis and mechanism insights
Gomes R.S., Jardim G.A., de Carvalho R.L., Araujo M.H., da Silva Júnior E.N.
Tetrahedron , 2019
240.
Strain and stereoelectronics in cycloalkyne click chemistry
Harris T., Alabugin I.V.
Mendeleev Communications , 2019
243.
Gold as a catalyst. Part I. Nucleophilic addition to the triple bond
Alyabyev S.B., Beletskaya I.P.
Russian Chemical Reviews , 2017
244.
Gold as a catalyst. Part II. Alkynes in the reactions of carbon - Carbon bond formation
Alyabyev S.B., Beletskaya I.P.
Russian Chemical Reviews , 2018
245.
Silver-catalysed reactions of alkynes: recent advances.
Fang G., Bi X.
Chemical Society Reviews , 2015
246.
Chemicals from Alkynes with Palladium Catalysts
Chinchilla R., Nájera C.
Chemical Reviews , 2013
247.
Recent Advances in Ruthenium(II)-Catalyzed C−H Bond Activation and Alkyne Annulation Reactions
Duarah G., Kaishap P.P., Begum T., Gogoi S.
Advanced Synthesis and Catalysis , 2018
252.
rcr_89_1_125bib252
Vasilyev
2018
253.
Directing-Group-mediated C-H-Alkynylations.
Caspers L.D., Nachtsheim B.J.
Chemistry - An Asian Journal , 2018
255.
Catalytic carbene/alkyne metathesis (CAM): a versatile strategy for alkyne bifunctionalization.
Pei C., Zhang C., Qian Y., Xu X.
Organic and Biomolecular Chemistry , 2018
257.
Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes.
Aggarwal T., Kumar S., Verma A.K.
Organic and Biomolecular Chemistry , 2016
258.
Alkyne Origami: Folding Oligoalkynes into Polyaromatics.
Alabugin I.V., Gonzalez-Rodriguez E.
Accounts of Chemical Research , 2018
259.
Cyclization of ortho-ethynylbiaryls as an emerging versatile tool for the construction of polycyclic arenes
Pankova A.S., Shestakov A.N., Kuznetsov M.A.
Russian Chemical Reviews , 2019
260.
Alkenylation of Arenes and Heteroarenes with Alkynes
Boyarskiy V.P., Ryabukhin D.S., Bokach N.A., Vasilyev A.V.
Chemical Reviews , 2016
262.
rcr_89_1_125bib262
Jesin
2019
264.
Allenation of Terminal Alkynes with Aldehydes and Ketones
Huang X., Ma S.
Accounts of Chemical Research , 2019
265.
Organocatalytic Oxidative Functionalizations of Alkynes
Patil D.V., Shin S.
Asian Journal of Organic Chemistry , 2018
266.
Conjugated enynones: preparation, properties and applications in organic synthesis
Golovanov A.A., Odin I.S., Zlotskii S.S.
Russian Chemical Reviews , 2019