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Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom

Roman Sergeevich Begunov 1
Roman Sergeevich Begunov
, 
Galina Aleksandrovna Ryzvanovich 1
Galina Aleksandrovna Ryzvanovich
1 P.G. Demidov Yaroslavl State University
Published 30 November 2012
Communication , Volume 82, Issue 1, 77-97
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Begunov R. S., Ryzvanovich G. A. Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom // Russian Chemical Reviews. 2013. Vol. 82. No. 1. pp. 77-97.
GOST all authors (up to 50)
Begunov R. S., Ryzvanovich G. A. Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom // Russian Chemical Reviews. 2013. Vol. 82. No. 1. pp. 77-97.
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TY - JOUR
DO - 10.1070/RC2013v082n01ABEH004295
UR - https://rcr.colab.ws/publications/10.1070/RC2013v082n01ABEH004295
TI - Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom
T2 - Russian Chemical Reviews
AU - Begunov, Roman Sergeevich
AU - Ryzvanovich, Galina Aleksandrovna
PY - 2013
DA - 2012/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 77-97
IS - 1
VL - 82
ER -
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@article{2013_Begunov,
author = {Roman Sergeevich Begunov and Galina Aleksandrovna Ryzvanovich},
title = {Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom},
journal = {Russian Chemical Reviews},
year = {2013},
volume = {82},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2013v082n01ABEH004295},
number = {1},
pages = {77--97},
doi = {10.1070/RC2013v082n01ABEH004295}
}
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Cite this
MLA
Begunov, Roman Sergeevich, and Galina Aleksandrovna Ryzvanovich. “Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom.” Russian Chemical Reviews, vol. 82, no. 1, Nov. 2013, pp. 77-97. https://rcr.colab.ws/publications/10.1070/RC2013v082n01ABEH004295.
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Abstract

The key methods of synthesis of fused imidazole derivatives with bridgehead nitrogen are systematized and described. The reaction mechanisms that form the basis of synthetic routes to pyrido[1,2-a]benzimidazoles and related structures are considered. The biological properties and biological action mechanisms of fused azaheterocycles are presented. Bibliography — 152 references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Zur Synthese und Struktur von 8-Nitro-imidazo [1,2-a]pyridinen
Sch�fer H., Gruner M., Gro�mann G., Gewald K.
Monatshefte fur Chemie , 1991
4.
Synthetic approaches to some new fluorescent dyestuffs for synthetic polymer fibres
Girges M.M., Hanna M.A., Ayyad S.N.
Pigment and Resin Technology , 1995
5.
5
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1953
6.
6
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
7.
Synthesis of Iso-C-nucleoside Analogues from 1-(Methyl 2-O-benzyl-4,6- O-benzylidene-3-deoxy-α-D-altropyranosid-3-yl)but-3-yn-2-ones
Otero I., Feist H., Michalik D., Michalik M., Quincoces J., Peseke K.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 2005
8.
Ring Transformations of 2-Formylglycals with C,N-Dinucleophiles
Montero A., Feist H., Michalik M., Quincoces J., Peseke K.
Synthesis , 2002
9.
Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues
Hashmi I.A., Feist H., Michalik M., Reinke H., Peseke K.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 2006
10.
Anellation and Ring Transformations of Push-pull-functionalized Deoxypyranosiduloses
Kordian M., Feist H., Peseke K.
Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences , 2009
11.
11
T. T. Bannister
Diss. Abstr. , 1959
12.
A new route to pyrimido[1,6-a]benzimidazole derivatives
Bakavoli M., Rahimizadeh M., Ebrahimi A.R., Taghizadeh A., Davoodnia A., Nikpour M.
Journal of Heterocyclic Chemistry , 2008
13.
Nouveaux dérivés tricycliques du benzimidazole
Guerret P., Langlois M.
Journal of Heterocyclic Chemistry , 1979
14.
14
V. B. Evstigneev
Zhur. Fiz. Khim. , 1958
15.
1-R-2-[(1E,3E)-4-Aminobuta-1,3-dien-1-yl]-1H-benzimidazoles. Synthesis and some transformations
Varlamov A.V., Komarova A.I., Levov A.N., Savitkina E.V., Krapivko A.P., Khrustalev V.N., Sorokina E.A., Kulikova L.N., Nikitina E.V., Zaytsev V.P., Zubkova F.I.
Russian Chemical Bulletin , 2010
16.
A Facile Synthesis of Pyrido [1,2-a] Benzimidazoles
RameshBabu V.N., NarahariBabu A., Anand V., Hanumanthu P.
Synthetic Communications , 1998
17.
Reaction of 2-aminobenzimidazole with bifunetional carboxylie acid derivatives. Formation of pyrimido[1,2-a] benzimidazolones
Chow A.W., Jakas D.R., Trotter B.P., Hall N.M., Hoover J.R.
Journal of Heterocyclic Chemistry , 1973
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
20.
A simple regioselective synthesis of pyrimido[1,2-a]benzimidazoles
Tseng S., Epstein J.W., Brabander H.J., Francisco G.
Journal of Heterocyclic Chemistry , 1987
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
26.
26
B. Ya. Dain
1957
27.
27
A. A. Krasnovskii
Biofizika , 1956
28.
A rapid and efficient method for synthesis of pyrimido[1,2-a]-benzimidazole derivatives under microwave irradiation
Zhuang Q., Li C., Tu S., Cao L., Zhou D., Shao Q., Guo C.
Journal of Heterocyclic Chemistry , 2008
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
32.
Polyfluorobenzoyl chlorides and isothiocyanates in reactions with CH-reactive benzimidazoles
Nosova E.V., Lipunova G.N., Laeva A.A., Charushin V.N.
Russian Chemical Bulletin , 2005
33.
Benzimidazole condensed ring systems.1. Syntheses and biological investigations of some substituted pyrido[1,2-a]benzimidazoles
Rida S.M., Soliman F.S., Badawey E.A., El-Ghazzawi E., Kader O., Kappe T.
Journal of Heterocyclic Chemistry , 1988
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
40.
Synthesis and X-ray crystal structure of pyrrolo[1,2-a]benzimidazoles
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1953
45.
Synthesis of New Heterocyclic Ring Systems via [1,3,5]Triazino[1,2-a]benzimidazole Derivatives
Primofiore G., Da Settimo F., Pardi G., Simorini F., La Motta C., Salemo S., Taliani S., Marini A.M.
Journal of Heterocyclic Chemistry , 2005
47.
47
G. Oster
"Research in Photosynthesis" , 1957
48.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
49.
Synthesis and structures of substituted 5,6-dihydro-spiro(benz[4,5]imidazo[1,2-c]quinazoline-6,3′-indolin)-2′-ones
Morozov P.G., Kurbatov S.V., Dolgushin F.M., Antipin M.Y., Olekhnovich L.P.
Russian Chemical Bulletin , 2004
54.
Photocyclisation of 1-styrylimidazoles. A novel route to N-bridgehead compounds
Cooper G., Irwin W.J.
Journal of the Chemical Society Perkin Transactions 1 , 1976
57.
Synthesis by Radical Cyclization and Cytotoxicity of Highly Potent Bioreductive Alicyclic Ring Fused [1,2-a]Benzimidazolequinones
Lynch M., Hehir S., Kavanagh P., Leech D., O'Shaughnessy J., Carty M., Aldabbagh F.
Chemistry - A European Journal , 2007
58.
58
N. E. Khomutov
1953
59.
Synthesis of New Trifluoromethyl Substituted 11H-Isoindolo[2,1-a]benzimidazol-11-one Derivatives
60.
Potential Anxiolytic Agents. Pyrido[1,2-a]benzimidazoles: A New Structural Class of Ligands for the Benzodiazepine Binding Site on GABA-A Receptors
Maryanoff B.E., Ho W., McComsey D.F., Reitz A.B., Grous P.P., Nortey S.O., Shank R.P., Dubinsky B., Taylor R.J., Gardocki J.F.
Journal of Medicinal Chemistry , 1995
61.
Process Research for the Synthesis of RWJ-51204, A Novel Anxiolytic Agent
Cohen J.H., Maryanoff C.A., Stefanick S.M., Sorgi K.L., Villani F.J.
Organic Process Research and Development , 1999
62.
Synthesis and application of imidazole derivatives synthesis of pyrido 1 2 a benzimidazolone derivatives
Ohta S., Yuasa T., Narita Y., Kawasaki I., Minamii E., Yamashita M.
Heterocycles , 1991
63.
63
1930
64.
243. Pyrido(1? : 2? : 1 : 2)benziminazoles and allied compounds (cyclic 1 : 3-diazalines)
Morgan G., Stewart J.
Journal of the Chemical Society (Resumed) , 1938
66.
A Novel Approach to the Synthesis of [1,2-a]Fused Polymethylenebenzimidazoles
Nazarenko K.G., Shyrokaya T.I., Shvidenko K.V., Tolmachev A.A.
Synthetic Communications , 2003
67.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
70.
Synthesis of pyrazino[1,2-a]benzimidazol-1(2H)ones via a microwave assisted Buchwald–Hartwig type reaction
Alen J., Robeyns K., De Borggraeve W.M., Van Meervelt L., Compernolle F.
Tetrahedron , 2008
73.
Synthesis of some substituted α-carbolines
Stephenson L., Warburton W.K.
Journal of the Chemical Society C Organic , 1970
75.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) , 1947
77.
77
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
78.
78
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
79.
79
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
80.
80
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1937
81.
Synthesis of azinoazole structural isomers by photocyclization
Frolov A.N.
Russian Journal of Organic Chemistry , 2006
83.
Synthesis of pyridazino[1,6-a]benzimidazoles
Benjamin L.E., Earley J.V., Gilman N.W.
Journal of Heterocyclic Chemistry , 1986
84.
84
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
86.
Thermische Umlagerung von Enaminen desPummerer-Ketons
Beck D., Schenker K.
Helvetica Chimica Acta , 1971
87.
87
J. F. Arens
"Advances in Organic Chemistry" , 1960
88.
88
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1946
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
90.
Simple synthesis of substituted benzo[4,5]imidazo[1,2-a]pyridines
Begunov R.S., Ryzvanovich G.A., Firgang S.I.
Russian Journal of Organic Chemistry , 2004
91.
Begunov Roman Sergeevich, Ryzvanovich Galina Aleksandrovna, Nozdracheva Ol'ga Igorevna
Mendeleev Communications , 2006
92.
Effect of hydrochloric acid on the reductive amination of 1-(3-nitropyridin-2-yl)pyridinium salts
93.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
94.
94
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
95.
95
A. A. Krasnovskii
Fiziologiya Rastenii , 1957
96.
96
L. M. Vorob'eva
Biokhimiya , 1958
97.
97
A. N. Terenin
Dokl. Akad. Nauk SSSR , 1952
99.
Reaktion von 2-Aminopyridin mit Chinonen
Schmid L., Czerny H.
Monatshefte fur Chemie , 1952
100.
Benzo [d] pyrido [a] benzimidazole-4,9-quinone
Truitt P., Cooper J.E., Wood F.M.
Journal of the American Chemical Society , 1957
104.
New rearrangements in the pyrolysis of nitrocarbodi-imides
Pipe D.F., Rees C.W.
Journal of the Chemical Society Chemical Communications , 1982
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR , 1958
106.
106
F. Fichter
Helv. Chim. Acta , 1927
107.
107
M. F. Shostakovskii
Zhur. Obshch. Khim. , 1961
108.
108
F. Fichter
Helv. Chim. Acta , 1924
109.
109
F. Ficher
Bull. Soc. chim. France (4) , 1916
110.
The reaction ofo-phenylenediamine with 3-methylglutaric anhydride
Lombardino J.G., Ewing F.E.
Journal of Heterocyclic Chemistry , 1982
111.
Synthesis of novel heterocycles with antimicrobial and surface activity
El-Sayed R., Wasfy A.A., Aly A.A.
Journal of Heterocyclic Chemistry , 2005
112.
Intramolecular reaction between nitro and carbodi-imide groups; a new synthesis of 2-arylbenzotriazoles
Houghton P.G., Pipe D.F., Rees C.W.
Journal of the Chemical Society Perkin Transactions 1 , 1985
117.
Pyrido[2′1′:2,3]imidazo[4,5-c]isoquinoline and the alkylation of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one
118.
118
V. M. Rodionov
Zhur. Obshch. Khim. , 1935
119.
119
V. V. Levchenko
Zhur. Obshch. Khim. , 1947
120.
Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives
Demirayak Ş., Abu Mohsen U., Çağri Karaburun A.
European Journal of Medicinal Chemistry , 2002
121.
121
V. V. Korshak
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
122.
122
S. R. Rafikov
Izv. Akad. Nauk SSSR, Otd. Khim. Nauk , 1953
123.
123
V. V. Levchenko
Zhur. Obshch. Khim. , 1952
125.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
126.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
127.
127
R. Pasternak
Helv. Chim. Acta , 1948
128.
5-Ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N- (2-fluorophenyl)carboxamide (RWJ-51204), a New Nonbenzodiazepine Anxiolytic
Dubinsky B., Vaidya A.H., Rosenthal D.I., Hochman C., Crooke J.J., DeLuca S., DeVine A., Cheo-Isaacs C.T., Carter A.R., Jordan A.D., Reitz A.B., Shank R.P.
Journal of Pharmacology and Experimental Therapeutics , 2002
130.
Potential anxiolytic agents. 2. Improvement of oral efficacy for the pyrido[1,2-a]benzimidazole (PBI) class of GABA-A receptor modulators
Maryanoff B.E., McComsey D.F., Ho W., Shank R.P., Dubinsky B.
Bioorganic and Medicinal Chemistry Letters , 1996
131.
131
N. Thooi
Compt. rend. , 1958
132.
132
G. Shima
Kyoto Univ. , 1929
133.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
134.
Potential antitumor agents. 54. Chromophore requirements for in vivo antitumor activity among the general class of linear tricyclic carboxamides
135.
Synthesis of new azino fused benzimidazolium salts. a new family of DNA intercalating agents. I
Pastor J., Siró J., García-Navío J., Vaquero J.J., Melia Rodrigo M., Ballesteros M., Alvarez-Builla J.
Bioorganic and Medicinal Chemistry Letters , 1995
138.
138
S. Ono
J. Chem. Soc. Japan , 1957
139.
Regioselective Synthesis of Pyrazolo[4,5-g]pyrido[1,2-a]benzimidazoles: Cytotoxic Derivatives of Pyrido[1,2-a]benzimidazolic Ring System.
DUPUY M., PINGIET F., BLACHE Y., CHAVIGNON O., TEULADE J., CHAPAT J.
Chemical and Pharmaceutical Bulletin , 2011
140.
140
1912
141.
141
Friedl.
142.
142
1913
143.
143
Friedl.
144.
144
1912
145.
Synthesis and structure-activity relationship of imidazo[1,2-a]benzimidazoles as corticotropin-releasing factor 1 receptor antagonists.
Han X., Pin S.S., Burris K., Fung L.K., Huang S., Taber M.T., Zhang J., Dubowchik G.M.
Bioorganic and Medicinal Chemistry Letters , 2005
146.
Synthesis and in Vitro Cytotoxic Evaluation of New Derivatives of Pyrido[1,2-a]benzimidazolic Ring System: The Pyrido[1',2':1,2]imidazo[4,5-h]quinazolines.
DUPUY M., PINGUET F., CHAVIGNON O., CHEZAL J., TEULADE J., CHAPAT J., BLACHE Y.
Chemical and Pharmaceutical Bulletin , 2002
147.
147
Y. Sasada
Acta Cryst. , 1898
148.
Antineoplastic activity of benzimidazo[1,2-b]-isoquinolines, indolo[2,3-b]quinolines, and pyridocarbazoles
Weinkauf R.L., Chen A.Y., Yu C., Liu L., Barrows L., LaVoie E.J.
Bioorganic and Medicinal Chemistry , 1994
149.
149
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1954
151.
Thiazolobenzimidazole: biological and biochemical anti-retroviral activity of a new nonnucleoside reverse transcriptase inhibitor.
Buckheit R.W., Hollingshead M.G., Germany-Decker J., White E.L., McMahon J.B., Allen L.B., Ross L.J., Don Decker W., Westbrook L., Shannon W.M., Weislow O., Bader J.P., Boyd M.R.
Antiviral Research , 1993
152.
152
W. Albert
Trans. Electrochem. Soc. , 1943
153.
Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation ofin vitro anti-HIV-1, anticancer and antimicrobial activities
154.
Synthesis of Pyrido[1,2-a]benzimidazoles through a Copper-Catalyzed Cascade C-N Coupling Process
Wu Z., Huang Q., Zhou X., Yu L., Li Z., Wu D.
European Journal of Organic Chemistry , 2011
155.
On the Importance of an Acid Additive in the Synthesis of Pyrido[1,2‐ a ]benzimidazoles by Direct Copper‐Catalyzed Amination
Masters K., Rauws T.R., Yadav A.K., Herrebout W.A., Van der Veken B., Maes B.U.
Chemistry - A European Journal , 2011
156.
156
J. S. Fruton
J. Biol. Med. , 1950
157.
Antimalarial Pyrido[1,2-a]benzimidazoles
Ndakala A.J., Gessner R.K., Gitari P.W., October N., White K.L., Hudson A., Fakorede F., Shackleford D.M., Kaiser M., Yeates C., Charman S.A., Chibale K.
Journal of Medicinal Chemistry , 2011