Home / Articles / Bipyrroles, furyl- and thienylpyrroles

Bipyrroles, furyl- and thienylpyrroles

Svetlana Evgenievna Korostova 1
Svetlana Evgenievna Korostova
, 
Albina Ivanovna Mikhaleva 1
Albina Ivanovna Mikhaleva
, 
1 A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences
Published 30 November 1998
Communication , Volume 68, Issue 6, 459-482
29
Share
Cite this
GOST
 | 
Cite this
GOST
Korostova S. E., Mikhaleva A. I., Trofimov B. A. Bipyrroles, furyl- and thienylpyrroles // Russian Chemical Reviews. 1999. Vol. 68. No. 6. pp. 459-482.
GOST all authors (up to 50)
Korostova S. E., Mikhaleva A. I., Trofimov B. A. Bipyrroles, furyl- and thienylpyrroles // Russian Chemical Reviews. 1999. Vol. 68. No. 6. pp. 459-482.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC1999v068n06ABEH000451
UR - https://rcr.colab.ws/publications/10.1070/RC1999v068n06ABEH000451
TI - Bipyrroles, furyl- and thienylpyrroles
T2 - Russian Chemical Reviews
AU - Korostova, Svetlana Evgenievna
AU - Mikhaleva, Albina Ivanovna
AU - Trofimov, Boris Aleksandrovich
PY - 1999
DA - 1998/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 459-482
IS - 6
VL - 68
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{1999_Korostova,
author = {Svetlana Evgenievna Korostova and Albina Ivanovna Mikhaleva and Boris Aleksandrovich Trofimov},
title = {Bipyrroles, furyl- and thienylpyrroles},
journal = {Russian Chemical Reviews},
year = {1999},
volume = {68},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC1999v068n06ABEH000451},
number = {6},
pages = {459--482},
doi = {10.1070/RC1999v068n06ABEH000451}
}
MLA
Cite this
MLA
Korostova, Svetlana Evgenievna, et al. “Bipyrroles, furyl- and thienylpyrroles.” Russian Chemical Reviews, vol. 68, no. 6, Nov. 1999, pp. 459-482. https://rcr.colab.ws/publications/10.1070/RC1999v068n06ABEH000451.
Views / Visits / Downloads
11 / 11 / 3

Abstract

Data on the methods of preparation of bipyrroles and furyl-, thienyl- and selenienylpyrroles are summarised and described systematically. The reactivity and the prospects of application of these compounds are discussed. Particular attention is paid to a new convenient one-step method for the synthesis of hetaryl-substituted pyrroles starting from alkyl hetaryl ketoximes and acetylene. The bibliography includes 191 references.

References

2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
5.
Prospects for the chemistry of pyrrole
Trofimov B.A.
Russian Chemical Reviews , 1989
6.
Polymerisation ofN-Vinylpyrroles
Trofimov B.A., Mikhaleva A.I., Morozova L.V.
Russian Chemical Reviews , 1985
7.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
9.
11
T. T. Bannister
Diss. Abstr. , 1959
10.
12
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
11.
Selenium-containing heterocycles
Litvinov V.P., Dyachenko V.D.
Russian Chemical Reviews , 1997
12.
15
A. S. Holt
"Research in Photosynthesis" , 1957
13.
16
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
14.
17
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1958
15.
Synthesis of pyrroles from aliphatic compounds
Sobenina L.N., Mikhaleva A.I., Trofimov B.A.
Russian Chemical Reviews , 1989
16.
Preparation of Pyrroles from Ketoximes and Acetylenes
Trofimov B.A.
Advances in Heterocyclic Chemistry , 1990
17.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
18.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
19.
Further development of the ketoxime-based pyrrole synthesis
A. Trofimov B., I. Mikhaleva A.
Heterocycles , 1994
20.
Sulfur-Containing Pyrroles
Trofimov B.A.
Phosphorus, Sulfur and Silicon and the Related Elements , 1994
21.
25
G. W. Robinson
J. Chem. Phys. , 1955
22.
26
B. Ya. Dain
1957
23.
27
A. A. Krasnovskii
Biofizika , 1956
24.
28
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
25.
29
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
26.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
27.
31
A. A. Krasnovskii
Biokhimiya , 1960
28.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
29.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
30.
34
G. W. Robinson
J. Chem. Phys. , 1886
31.
35
Z. K. Maizus
Dokl. Akad. Nauk SSSR , 1960
32.
36
J. Billon
Bull. Soc. chim. France , 1960
33.
37
L. M. Kosobutskaya
Dokl. Akad. Nauk SSSR , 1950
34.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
35.
39
V. F. Gachkovskii
Biofizika , 1959
36.
40
A. A. Krasnovskii
Biofizika , 1960
37.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
38.
42
L. K. Obukhova
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
39.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
40.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
41.
45
W. Hendrich
Roczniki Chemii , 1958
42.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
43.
47
G. Oster
"Research in Photosynthesis" , 1957
44.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
45.
49
A. A. Krasnovskii
Biofizika , 1958
46.
50
G. Glacomello
Gazzetta. , 1935
47.
51
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1954
48.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
49.
53
D. Porretand E. Rabinowitch
Nature , 1937
50.
54
R. Livingston
J. Phys. Chem. , 1941
51.
55
G. A. Bogdanovskii
1958
52.
Protecting groups for the pyrrole nitrogen atom. The 2-chloroethyl, 2-phenylsulfonylethyl, and related moieties
Gonzalez C., Greenhouse R., Tallabs R., Muchowski J.M.
Canadian Journal of Chemistry , 1983
53.
57
R. Livingston
"Research in Photosynthesis" , 1957
54.
58
N. E. Khomutov
1953
55.
59
H. Linshitz
"Research in Photosynthesis" , 1957
56.
60
A. N. Terenin
Optika i Spektrosk. , 1956
57.
61
A. N. Terenin
1959
58.
62
A. A. Krasnovskii
"Sbornik, Voprosy Khimicheskoi Kinetiki" (Symposium, Problems of Chemical Kinetics) , 1955
59.
63
1930
60.
A synthesis of pyrrole derivatives from O-(2-hydroxyethyl)-ketoximes
Dhanak D., Reese C.B., Romana S., Zappia G.
Journal of the Chemical Society Chemical Communications , 1986
61.
65
A. A. Krasnovskii
Biofizika , 1959
62.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
63.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
64.
68
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1946
66.
70
N. Bubnov
Biofizika , 1960
67.
71
Yu. A. Shlyapnikov
Vysokomol. Soed. , 1962
68.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
69.
Synthese der 5-Arylpyrromethene
Berner H., Schulz G., Reinshagen H.
Monatshefte fur Chemie , 1977
70.
Four novel phenyldithienoindole isomers from the oxidative photocyclization of dithienylpyrroles
Perrine D.M., Kagan J., Huang D.B., Zeng K., Teo B.K.
Journal of Organic Chemistry , 1987
72.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
73.
Eine bequeme Synthese von 2-Aroyl-5-arylpyrrolen
74.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
75.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
77.
81
J. C. Ghosh
J. Indian Chem. Soc. , 1934
78.
82
G. P. Brin
Biokhimiya , 1957
79.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
80.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
82.
Synthesis and cycloaddition reactions of 2-(2-thienyl)aziridines
Lown J.W., Matsumoto K.
Canadian Journal of Chemistry , 1970
83.
1,3-Dipolar cycloaddition reactions of 2-(2′-thienyl)aziridines
Lown J.W., Matsumoto K.
Canadian Journal of Chemistry , 1970
84.
Eine neue Pyrrolsynthese aus Butadiin‐Derivaten
Schulte K.E., Reisch J., Walker H.
Chemische Berichte , 1965
85.
Synthesis of substituted pyrroles via zirconocene complexes of imines
Buchwald S.L., Wannamaker M.W., Watson B.T.
Journal of the American Chemical Society , 1989
88.
92
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
89.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
90.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
91.
Syntheses of 3-substituted pyrrole derivatives with antiinflammatory activity.
SAKAI K., SUZUKI M., NUNAMI K., YONEDA N., ONODA Y., IWASAWA Y.
Chemical and Pharmaceutical Bulletin , 2011
93.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
94.
98
W. Franke
Chem. Zentr. , 1954
95.
99
V. V. Zolotarev
1938
96.
100
V. V. Zolotarev
Chem. Abs. , 1941
97.
101
M. F. Shostakovskii
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1960
98.
102
F. Fichter
Helv. Chim. Acta , 1922
99.
103
L. N. Bell
Dokl. Akad. Nauk SSSR , 1956
102.
N-(Triisopropylsilyl)pyrrole. A progenitor "par excellence" of 3-substituted pyrroles
Bray B.L., Mathies P.H., Naef R., Solas D.R., Tidwell T.T., Artis D.R., Muchowski J.M.
Journal of Organic Chemistry , 1990
103.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
104.
Gjøs N., Gronowitz S., Welch B.J., Prelesnik A., Zupancic I., Ehrenberg L.
Acta Chemica Scandinavica , 2008
105.
Oligoheterocycles by the Stille-coupling reaction
Groenendaal L., Peerlings H.W., Havinga E.E., Vekemans J.A., Meijer E.W.
Synthetic Metals , 1995
107.
111
M. Calvin
1956
108.
A general method for the synthesis of 2-arylpyrroles
Boukou-Poba J.P., Farnier M., Guilard R.
Tetrahedron Letters , 1979
109.
2,2″-Bipyrrole
Rapoport H., Castagnoli N.
Journal of the American Chemical Society , 1962
110.
The Synthesis of Prodigiosin
Rapoport H., Holden K.G.
Journal of the American Chemical Society , 1962
111.
2,2':5',2″-Terpyrrole1a
Rapoport H., Castagnoli N., Holden K.G.
Journal of Organic Chemistry , 1964
112.
Synthesis of Substituted 2,2'-Bipyrroles1a
Rapoport H., Bordner J.
Journal of Organic Chemistry , 1964
113.
Synthesis of 2,2'-Bipyrroles from 2-Pyrrolinones1a
Bordner J., Rapoport H.
Journal of Organic Chemistry , 1965
117.
Synthesis of 5,6-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-f][1,4]diazepines †‡
118.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
119.
New Condensed Triheterocyclic Systems; Pyrrolothienopyrazines
Robba M., Rault S., Cugnon de Sévricourt M.
Heterocycles , 1980
120.
124
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
121.
Synthese von prodigiosin-analogen
Kresze G., Morper M., Bijev A.
Tetrahedron Letters , 1977
123.
Acid-catalyzed cyclization of chalcones derived from various nitrogenous heteroaromatic compounds.
MATOBA K., ITOH K., KONDO K., YAMAZAKI T., NAGATA M.
Chemical and Pharmaceutical Bulletin , 2011
124.
The base-catalysed cyclisations of 1,19-dideoxybiladienes-ac
Dolphin D., Johnson A.W., Leng J., Broek P.V.
Journal of the Chemical Society C Organic , 1966
125.
Sulphur extrusion reactions applied to the synthesis of corroles and related systems
Broadhurst M.J., Grigg R., Johnson A.W.
Journal of the Chemical Society Perkin Transactions 1 , 1972
126.
Recent Advances in the Chemistry of Pyrrole.
Baltazzi E., Krimen L.I.
Chemical Reviews , 1963
128.
132
G. Shima
Kyoto Univ. , 1929
129.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
130.
134
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1948
131.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1945
132.
136
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1954
133.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
134.
138
S. Ono
J. Chem. Soc. Japan , 1957
135.
139
I. L. Knunyants
1959
136.
140
1912
137.
Protonated forms of 2-(2-furyl)pyrroles and their interconversion: proton NMR and quantum-chemical (MNDO) study
Sigalov M.V., Schmidt E.Y., Trofimov A.B., Trofimov B.A.
Journal of Organic Chemistry , 1992
138.
Protonation of 2-(2-thienyl)pyrrole and 2-(2-thienyl)-1-vinylpyrroles
Sigalov M.V., Trofimov A.B., Shmidt E.Y., Trofimov B.A.
Journal of Physical Organic Chemistry , 1993
139.
143
Friedl.
140.
144
1912
141.
145
Friedl.
142.
Formylation en série arylpyrrolique
Boukou-Poba J., Farnier M., Guilard R.
Canadian Journal of Chemistry , 1981
145.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
147.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
148.
152
W. Albert
Trans. Electrochem. Soc. , 1943
151.
155
M. V. Mal'tsev
Izv. Vys. Ucheb. Zaved., Tsvet. Met. , 1960
152.
156
J. S. Fruton
J. Biol. Med. , 1950
153.
157
1903
154.
158
Friedl.
155.
159
J. Tafel
Z. Elektrochem. , 1911
156.
160
1912
157.
161
Friedl.
158.
ELECTROPHILIC SUBSTITUTIONS OF OLEFINIC HYDROGENS II. ACYLATION OF VINYL ETHERS AND N-VINYL AMIDES
Hojo M., Masuda R., Kokuryo Y., Shioda H., Matsuo S.
Chemistry Letters , 1976
159.
163
Friedl.
160.
164
1917
161.
165
Friedl.
162.
166
1917
163.
167
Friedl.
164.
168
1918
165.
169
Friedl.
166.
170
1918
167.
171
Friedl.
168.
The Equilibrium NH Acidity of Organic Compounds
169.
173
Friedl.
170.
174
S. Calvert
India Rubber Tire Rev. , 1926
171.
175
I. Mayer
1966
172.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
173.
177
J. Henry
Proc. R. Irish Acad. , 1945
174.
178
1946
175.
Synthesis and Characterization of New "Expanded" Thiophene- and Furan-Containing Macrocycles
Miller D.C., Johnson M.R., Ibers J.A.
Journal of Organic Chemistry , 1994
176.
180
1946
177.
628. Bipyrroles. Part III
Grigg R., Johnson A.W.
Journal of the Chemical Society (Resumed) , 1964
178.
182
1947
179.
183
Chem. Abs. , 1947
180.
Catalytic hydrogenation of pyrroles at atmospheric pressure
Kaiser H.P., Muchowski J.M.
Journal of Organic Chemistry , 1984
181.
185
1954
182.
Reduction of heterocycles with nickel-aluminum alloy
183.
187
1954
184.
188
Chem. Abs. , 1955
185.
189
M. Godchot
Bull. Soc. chim. France (5) , 1913
186.
190
H. Law
J. Chem. Soc. , 1912
187.
191
M. Matsui
Mem. Coll. Sci., Kyoto Univ. , 1920
188.
Synthese neuer 3-substituierter Pyrrole
Stefan K., Schuhmann W., Parlar H., Korte F.
Chemische Berichte , 1989
189.
193
E. Pannain
Gazzetta , 1909
192.
196
E. Müller
Z. Elektrochem. , 1910
193.
197
J. Sicher
Chem. Listy , 1955
195.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
196.
200
Ref. Zh. Khim. , 1975
197.
201
A. Aladjem
1969
198.
202
G. Shiroa
Mem. Coll. Sci., Kyoto Univ. , 1930
199.
203
L. Andrieux
Compt. rend. , 1929
200.
Stabilization of n‐Si Photoanodes to Surface Corrosion in Aqueous Electrolyte with a Thin Film of Polypyrrole
Skotheim T., Lundström I., Prejza J.
Journal of the Electrochemical Society , 1981
201.
Electrochemical Formation of Polypyrrole/ SiO2 Composite Film and Its Application to Organic Electroluminescence Devices
Komaba S., Fujihana K., Osaka T., Aiki S., Nakamura S.
Journal of the Electrochemical Society , 1998
202.
206
J. Petersen
Z. Phys. Chem. , 1900
204.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956