Home / Articles / C-Ethynylpyrroles: synthesis and reactivity

C-Ethynylpyrroles: synthesis and reactivity

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Denis Nikolaevich Tomilin 1
Denis Nikolaevich Tomilin
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1 A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Published 30 November 2013
Communication , Volume 83, Issue 6, 475-501
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Sobenina L. N., Tomilin D. N., Trofimov B. A. C-Ethynylpyrroles: synthesis and reactivity // Russian Chemical Reviews. 2014. Vol. 83. No. 6. pp. 475-501.
GOST all authors (up to 50)
Sobenina L. N., Tomilin D. N., Trofimov B. A. C-Ethynylpyrroles: synthesis and reactivity // Russian Chemical Reviews. 2014. Vol. 83. No. 6. pp. 475-501.
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TY - JOUR
DO - 10.1070/RC2014v083n06ABEH004418
UR - https://rcr.colab.ws/publications/10.1070/RC2014v083n06ABEH004418
TI - C-Ethynylpyrroles: synthesis and reactivity
T2 - Russian Chemical Reviews
AU - Sobenina, Lyubov Nikolaevna
AU - Tomilin, Denis Nikolaevich
AU - Trofimov, Boris Aleksandrovich
PY - 2014
DA - 2013/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 475-501
IS - 6
VL - 83
ER -
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@article{2014_Sobenina,
author = {Lyubov Nikolaevna Sobenina and Denis Nikolaevich Tomilin and Boris Aleksandrovich Trofimov},
title = {C-Ethynylpyrroles: synthesis and reactivity},
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/RC2014v083n06ABEH004418},
number = {6},
pages = {475--501},
doi = {10.1070/RC2014v083n06ABEH004418}
}
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Sobenina, Lyubov Nikolaevna, et al. “C-Ethynylpyrroles: synthesis and reactivity.” Russian Chemical Reviews, vol. 83, no. 6, Nov. 2014, pp. 475-501. https://rcr.colab.ws/publications/10.1070/RC2014v083n06ABEH004418.
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Abstract

The principal methods for the synthesis of C-ethynylpyrroles are presented. The mechanisms of reactions underlying these methods are considered. The reactivity of C-ethynylpyrroles is discussed with primary attention being given to cycloaddition and intramolecular cyclization involving the ethynyl substituent, resulting in new pyrrole systems.

Bibliography --- 131 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
Formation of pyrrolylacetylene by vilsmeier formylation of 3-methyl-4-acetylpyrrole
Mironov A.F., Akimenko L.V., Rumyantseva V.D., Evstigneeva R.P.
Chemistry of Heterocyclic Compounds , 1975
7.
7
E. Rabinowitch
"Photosynthesis" , 1956
8.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
A New, Convenient Synthesis of Pyrrolylacetylenes
Mironov A.F., Kozhich D.T., Vasilevsky V.I., Evstigneeva R.P.
Synthesis , 1979
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
13.
Syntheses of some β-substituted alkyne porphyrins related to protoporphyrin-IX
Jiang X., Smith K.M.
Journal of the Chemical Society Perkin Transactions 1 , 1996
14.
Synthesis of functionalizedN-methylpyrroles
Barrero A.F., Sánchez J.F., Oltra J.E., Teva D.
Journal of Heterocyclic Chemistry , 1991
17.
Synthesis and unexpectedly facile dimerisation of 1-methoxycarbonylpyrrolizin-3-one
Comer M.C., Despinoy X.L., Gould R.O., McNab H., Parsons S.
Chemical Communications , 1996
18.
1-Methoxycarbonylpyrrolizin-3-one and related compounds
Despinoy X.L., McNab H.
Organic and Biomolecular Chemistry , 2009
20.
20
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
22.
Gold-Catalyzed Ethynylation of Arenes
de Haro T., Nevado C.
Journal of the American Chemical Society , 2010
24.
Ethynylation of pyrroles with 1-acyl-2-bromoacetylenes on alumina: a formal ‘inverse Sonogashira coupling’
Trofimov B.A., Stepanova Z.V., Sobenina L.N., Mikhaleva A.I., Ushakov I.A.
Tetrahedron Letters , 2004
25.
Synthesis of 2-benzoylethynylpyrroles by cross coupling of 2-arylpyrroles with 1-benzoyl-2-bromoacetylene over aluminum oxide
Trofimov B.A., Sobenina L.N., Stepanova Z.V., Demenev A.P., Mikhaleva A.I., Ushakov I.A., Vakul’skaya T.I., Petrova O.V.
Russian Journal of Organic Chemistry , 2006
26.
27
A. A. Krasnovskii
Biofizika , 1956
27.
Pyrroles and N-Vinylpyrroles from Ketones and Acetylenes
Trofimov B.A., Mikhaleva A.I., Schmidt E.Y., Sobenina L.N.
Advances in Heterocyclic Chemistry , 2010
28.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
29.
Synthesis of 3-[5-(biphenyl-4-yl)pyrrol-2-yl]-1-phenylprop-2-yn-1-ones by palladium-free cross-coupling between pyrroles and haloalkynes on aluminum oxide
Sobenina L.N., Stepanova Z.V., Petrova O.V., Ma J.S., Yang G., Tatarinova A.A., Mikhaleva A.I., Trofimov B.A.
Russian Chemical Bulletin , 2013
30.
Regioselective Cross-Coupling of 1-Vinylpyrroles with Acylbromoacetylenes on Al2O3: Synthesis of 2-(2-Acylethynyl)-1-vinylpyrroles
Trofimov B., Sobenina L., Stepanova Z., Ushakov I., Petrova O., Tarasova O., Volkova K., Mikhaleva A.
Synthesis , 2007
31.
A palladium- and copper-free cross-coupling of ethyl 3-halo-2-propynoates with 4,5,6,7-tetrahydroindoles on alumina
Trofimov B.A., Sobenina L.N., Demenev A.P., Stepanova Z.V., Petrova O.V., Ushakov I.A., Mikhaleva A.I.
Tetrahedron Letters , 2007
32.
Reactions of 2-phenylpyrrole with bromobenzoylacetylene on metal oxides active surfaces
Trofimov B.A., Sobenina L.N., Stepanova Z.V., Vakul'skaya T.I., Kazheva O.N., Aleksandrov G.G., Dyachenko O.A., Mikhaleva A.I.
Tetrahedron , 2008
33.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
34.
Trofimov Boris Aleksandrovich, Stepanova Zinaida Vasil'evna, Sobenina Lyubov Nikolaevna, Mikhaleva Albina Ivanovna, Sinegovskaya Lidia Mikhailovna, Potekhin Konstantin Albertovich, Fedyanin Ivan Vladimirovich
Mendeleev Communications , 2005
35.
Cross-coupling of 4,5,6,7-tetrahydroindole with functionalized haloacetylenes on active surfaces of metal oxides and salts
Sobenina L.N., Tomilin D.N., Petrova O.V., Gulia N., Osowska K., Szafert S., Mikhaleva A.I., Trofimov B.A.
Russian Journal of Organic Chemistry , 2010
36.
Chemo- and regioselective ethynylation of 4,5,6,7-tetrahydroindoles with ethyl 3-halo-2-propynoates
Trofimov B.A., Sobenina L.N., Stepanova Z.V., Petrova O.V., Ushakov I.A., Mikhaleva A.I.
Tetrahedron Letters , 2008
37.
Ethynylation of indoles with 1-benzoyl-2-bromoacetylene on Al2O3
Sobenina L.N., Demenev A.P., Mikhaleva A.I., Ushakov I.A., Vasil’tsov A.M., Ivanov A.V., Trofimov B.A.
Tetrahedron Letters , 2006
38.
Reaction of indoles with ethyl bromopropynoate over Al2O3 surface
Petrova O.V., Sobenina L.N., Ushakov I.A., Mikhaleva A.I.
Russian Journal of Organic Chemistry , 2008
39.
Preparation of ethyl arylpropiolates from aryl iodides by palladium-catalyzed cross-coupling reaction
Sakamoto T., Shiga F., Yasuhara A., Uchiyama D., Kondo Y., Yamanaka H.
Synthesis , 1992
41.
Preparation of 1-Aryl- or 1-Alkenyl-2-(perfluoroalkyl)acetylenes
Yoneda N., Matsuoka S., Miyaura N., Fukuhara T., Suzuki A.
Bulletin of the Chemical Society of Japan , 1990
42.
Convenient synthesis of methyl indol-2-ylpropiolate
Passarella D., Lesma G., Deleo M., Martinelli M., Silvani A.
Journal of the Chemical Society Perkin Transactions 1 , 1999
44.
Direct Palladium-Catalyzed Alkynylation of N-Fused Heterocycles
Seregin I.V., Ryabova V., Gevorgyan V.
Journal of the American Chemical Society , 2007
45.
Direct alkynylation of indole and pyrrole heterocycles.
Brand J., Charpentier J., Waser J.
Angewandte Chemie - International Edition , 2009
46.
4-Halogeno-1,1,1-trifluorobut-3-yn-2-one [4+2] cycloadducts and their cross-coupling with organozinc compounds
Koldobskii A.B., Tsvetkov N.P., Shilova O.S., Solodova E.V., Kalinin V.N.
Russian Chemical Bulletin , 2009
47.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
51.
Oxidative Radical Cyclization of (.omega.-Iodoalkyl)indoles and Pyrroles. Synthesis of (-)-Monomorine and Three Diastereomers
54.
An improved synthesis of the C,D-ring pyrromethenone of phytochrome and phytochromobilin
56.
New Strategies for the Synthesis of Biologically Important Tetrapyrroles. The “B,C + D + A” Approach to Linear Tetrapyrroles
57.
New Syntheses of the C,D-Ring Pyrromethenones of Phytochrome and Phycocyanin
Jacobi P.A., DeSimone R.W., Ghosh I., Guo J., Leung S.H., Pippin D.
Journal of Organic Chemistry , 2000
59.
Discovery of subtype-selective NMDA receptor ligands: 4-Benzyl-1-piperidinylalkynylpyrroles, pyrazoles and imidazoles as NR1a/2B antagonists
Wright J.L., Gregory T.F., Boxer P.A., Meltzer L.T., Serpa K.A., Wise L.D., Hong-Bae S., Huang J.C., Konkoy C.S., Upasani R.B., Whittemore E.R., Woodward R.M., Yang K.C., Zhou Z.
Bioorganic and Medicinal Chemistry Letters , 1999
61.
2,7-Bis(1H-pyrrol-2-yl)ethynyl-1,8naphthyridine:  An Ultrasensitive Fluorescent Probe for Glucopyranoside
Liao J., Chen C., Chou H., Cheng C., Chou P., Fang J., Slanina Z., Chow T.J.
Organic Letters , 2002
62.
Anthracene-BODIPY cassettes: syntheses and energy transfer.
Wan C., Burghart A., Chen J., Bergström F., Johansson L.B., Wolford M.F., Kim T.G., Topp M.R., Hochstrasser R.M., Burgess K.
Chemistry - A European Journal , 2003
65.
Synthesis of acetylenic derivatives of pyrrole
Vasilevskii S.F., Sundukova T.A., Shvartsberg M.S., Kotlyarevskii I.L.
Russian Chemical Bulletin , 1979
66.
70
N. Bubnov
Biofizika , 1960
67.
Synthesis of acetylenyl-N-methylpyrroles
Vasilevskii S.F., Sundukova T.A., Shvartsberg M.S., Kotlyarevskii I.L.
Russian Chemical Bulletin , 1980
68.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
70.
Highly Regioselective Synthesis of 3,4-Disubstituted 1H-Pyrrole,1
Liu J., Chan H., Wong H.N.
Journal of Organic Chemistry , 2000
71.
Synthesis of 3-arylpyrroles and 3-pyrrolylacetylenes by palladium-catalyzed coupling reactions
Alvarez A., Guzman A., Ruiz A., Velarde E., Muchowski J.M.
Journal of Organic Chemistry , 1992
72.
5-Methyl-1-phenylpyrrolo[3,4-d]borepin: a polarized aromatic molecule
Sugihara Y., Miyatake R., Murata I., Imamura A.
Journal of the Chemical Society Chemical Communications , 1995
73.
A new bipyrrole coupling reaction
Nikitin E.B., Nelson M.J., Lightner D.A.
Journal of Heterocyclic Chemistry , 2007
75.
Synthetic Chlorins Bearing Auxochromes at the 3- and 13-Positions
Laha J.K., Muthiah C., Taniguchi M., McDowell B.E., Ptaszek M., Lindsey J.S.
Journal of Organic Chemistry , 2006
79.
An unnatural hydrophobic base, 4-propynylpyrrole-2-carbaldehyde, as an efficient pairing partner of 9-methylimidazo[(4,5)- b ]pyridine
80.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
81.
Photophysics and photochemistry of 22.pi. and 26.pi. acetylene-cumulene porphyrinoids
Martire D.O., Jux N., Aramendia P.F., Martin Negri R., Lex J., Braslavsky S.E., Schaffner K., Vogel E.
Journal of the American Chemical Society , 1992
83.
A new class of linear tetrapyrroles: acetylenic 10,10a-didehydro-10a-homobilirubins.
Tu B., Ghosh B., Lightner D.A.
Journal of Organic Chemistry , 2003
84.
Novel Linear Tetrapyrroles: Hydrogen Bonding in Diacetylenic Bilirubins
Tu B., Ghosh B., Lightner D.A.
Monatshefte fur Chemie , 2004
85.
A novel diacetylenic bilirubin
Tu B.B., Lightner D.A.
Journal of Heterocyclic Chemistry , 2003
87.
Synthesis and photochromic behaviour of new dipyrrolylperfluorocyclopentenes
Heynderickx A., Mohamed Kaou A., Moustrou C., Samat A., Guglielmetti R.
New Journal of Chemistry , 2003
88.
Thermal reversibility and bistability in photochromic diarylethenes
Favaro G., Mazzucato U., Ortica F., Smimmo P.
Inorganica Chimica Acta , 2007
89.
Dibenzyl 3,3′,4,4′-tetramethyl-5,5′-(ethynediyl)bis(pyrrole-2-carboxylate)
Tanui H.K., Fronczek F.R., Vicente M.G.
Acta Crystallographica Section E Structure Reports Online , 2007
90.
Efficient synthesis and reactions of 1,2-dipyrrolylethynes
Tanui H.K., Hao E., Ihachi M.I., Fronczek F.R., Smith K.M., Vicente M.G.
Journal of Porphyrins and Phthalocyanines , 2011
91.
Bis(1-tosyl-2-pyrrolyl)ethyne
Tanui H.K., Fronczek F.R., Vicente M.G.
Acta Crystallographica Section E Structure Reports Online , 2007
93.
Jux N., Koch P., Schmickler H., Lex J., Vogel E.
1990
95.
99
V. V. Zolotarev
1938
96.
100
V. V. Zolotarev
Chem. Abs. , 1941
101.
1,3-Dipolar cycloaddition of azomethine ylides derived from imines and difluorocarbene to alkynes: A new active Pb-mediated approach to 2-fluoropyrrole derivatives
Novikov M.S., Khlebnikov A.F., Sidorina E.S., Kostikov R.R.
Journal of the Chemical Society Perkin Transactions 1 , 2000
102.
A New Neoclerodane Diterpenoid from Scutellaria hematochlora
Takeda Y., Tateoka S., Masuda T., Otsuka H., Honda G., Takaishi Y., Ito M., K. Khodzhimatov O., A. Ashurmetov O.
Heterocycles , 2001
104.
A general approach to polysubstituted pyrroles
Knight D.W., Rost H.C., Sharland C.M., Singkhonrat J.
Tetrahedron Letters , 2007
105.
Development of a New Approach to Pyrrole Ring Formation: First Example of a 3-(1-Alkynyl)-2-(alkylthio)pyrroles
106.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR , 1960
108.
Unusually sluggish copper(I)catalyzed oxidative dimerization of 2-ethynyl-1-methylpyrrole
Vasilevsky S.F., Verkruijsse H.D., Brandsma L.
Recueil des Travaux Chimiques des Pays-Bas , 2010
110.
Formal Synthesis of (±)-Roseophilin
Bitar A.Y., Frontier A.J.
Organic Letters , 2008
112.
116
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
113.
Von Porphyrin‐Isomeren zu octapyrrolischen Makrocyclen mit 8er‐Konformation
Vogel E., Bröring M., Fink J., Rosen D., Schmickler H., Lex J., Chan K.W., Wu Y., Nendel M., Plattner D.A., Houk K.N.
Angewandte Chemie , 1995
116.
120
V. V. Levchenko
Zhur. Obshch. Khim. , 1948
117.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
118.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
120.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
121.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
124.
Facile [2+2] Cycloaddition of DDQ to an Alkyne: Synthesis of Pyrrolyl- and Indolylbicyclo[4.2.0]octadienes from C-Ethynylpyrroles or C-Ethynylindoles
Trofimov B., Sobenina L., Stepanova Z., Ushakov I., Sinegovskaya L., Vakul’skaya T., Mikhaleva A.
Synthesis , 2009
125.
From 4,5,6,7-tetrahydroindole to functionalized furan-2-one–4,5,6,7-tetrahydroindole–cyclobutene sequence in two steps
Sobenina L.N., Stepanova Z.V., Ushakov I.A., Mikhaleva A.I., Tomilin D.N., Kazheva O.N., Alexandrov G.G., Dyachenko O.A., Trofimov B.A.
Tetrahedron , 2011
126.
Rearrangements of the [2+2]-cycloadducts of DDQ and 2-ethynylpyrroles
Trofimov B.A., Sobenina L.N., Stepanova Z.V., Ushakov I.A., Mikhaleva A.I., Tomilin D.N., Kazheva O.N., Alexandrov G.G., Chekhlov A.N., Dyachenko O.A.
Tetrahedron Letters , 2010
127.
Click Chemistry with 2-Ethynyl-4,5,6,7-tetrahydroindoles: Towards Functionalized Tetrahydroindole-Triazole Ensembles
Trofimov B., Sobenina L., Tomilin D., Ushakov I., Mikhaleva A., Ma J., Yang G.
Synthesis , 2013
128.
Regio- and Stereoselective Synthesis of Cyclopentenones: Intermolecular Pseudo-Pauson-Khand Cyclization
Barluenga J., Álvarez-Fernández A., Suárez-Sobrino Á.L., Tomás M.
Angewandte Chemie - International Edition , 2011
129.
One-Pot Synthesis of Metalated Pyridines from Two Acetylenes, a Nitrile, and a Titanium(II) Alkoxide
Tanaka R., Yuza A., Watai Y., Suzuki D., Takayama Y., Sato F., Urabe H.
Journal of the American Chemical Society , 2005
132.
Synthesis of Aromatic Ketones by a Transition Metal-Catalyzed Tandem Sequence
Zhao J., Hughes C.O., Toste F.D.
Journal of the American Chemical Society , 2006
136.
Synthesis of 5-alkoxy-2-alkylthio-3-pyrrol-2-ylpyrroles
Brandsma L., Nedolya N.A., Verkruijsse H.D., Trofimov B.A.
Chemistry of Heterocyclic Compounds , 2000
137.
141
Friedl.
138.
Chirality Transfer in Gold-Catalyzed Carbothiolation of o-Alkynylphenyl 1-Arylethyl Sulfides