Benzimidazoles and related heterocycles 10. A novel acid-catalyzed rearrangement in the system 3-(α-aminobenzyl)quinoxalin-2(1H)-one-ethyl acetoacetate as a simple and efficient method for synthesizing 2-(pyrrol-3-yl)benzimidazoles
V A Mamedov
1
,
E A Khafizova
1
,
A.T. Gubaidullin
1
,
A M Murtazina
1
,
D I Adgamova
1
,
A I Samigullina
1
,
I A Litvinov
1
Publication type: Journal Article
Publication date: 2011-02-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
A reaction of 3-(α-aminobenzyl)quinoxalin-2(1H)-one with ethyl acetoacetate in boiling acetic acid is accompanied by contraction of the pyrazine ring. A rearrangement involving the fragment C(2)-C(3)-C(NH2)Ph of the quinoxaline system and the fragment C(2)-C(3) of ethyl acetoacetate yields 2-(4-ethoxycarbonyl-5-methyl-2-phenylpyrrol-3-yl)benzimidazole. Possible pathways of this reaction are considered.
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11
Total citations:
11
Citations from 2024:
2
(18.18%)
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Mamedov V. A. et al. Benzimidazoles and related heterocycles 10. A novel acid-catalyzed rearrangement in the system 3-(α-aminobenzyl)quinoxalin-2(1H)-one-ethyl acetoacetate as a simple and efficient method for synthesizing 2-(pyrrol-3-yl)benzimidazoles // Russian Chemical Bulletin. 2011. Vol. 60. No. 2. pp. 368-372.
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Mamedov V. A., Khafizova E. A., Gubaidullin A., Murtazina A. M., Adgamova D. I., Samigullina A. I., Litvinov I. A. Benzimidazoles and related heterocycles 10. A novel acid-catalyzed rearrangement in the system 3-(α-aminobenzyl)quinoxalin-2(1H)-one-ethyl acetoacetate as a simple and efficient method for synthesizing 2-(pyrrol-3-yl)benzimidazoles // Russian Chemical Bulletin. 2011. Vol. 60. No. 2. pp. 368-372.
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TY - JOUR
DO - 10.1007/s11172-011-0059-1
UR - https://doi.org/10.1007/s11172-011-0059-1
TI - Benzimidazoles and related heterocycles 10. A novel acid-catalyzed rearrangement in the system 3-(α-aminobenzyl)quinoxalin-2(1H)-one-ethyl acetoacetate as a simple and efficient method for synthesizing 2-(pyrrol-3-yl)benzimidazoles
T2 - Russian Chemical Bulletin
AU - Mamedov, V A
AU - Khafizova, E A
AU - Gubaidullin, A.T.
AU - Murtazina, A M
AU - Adgamova, D I
AU - Samigullina, A I
AU - Litvinov, I A
PY - 2011
DA - 2011/02/01
PB - Springer Nature
SP - 368-372
IS - 2
VL - 60
SN - 1066-5285
SN - 1573-9171
ER -
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BibTex (up to 50 authors)
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@article{2011_Mamedov,
author = {V A Mamedov and E A Khafizova and A.T. Gubaidullin and A M Murtazina and D I Adgamova and A I Samigullina and I A Litvinov},
title = {Benzimidazoles and related heterocycles 10. A novel acid-catalyzed rearrangement in the system 3-(α-aminobenzyl)quinoxalin-2(1H)-one-ethyl acetoacetate as a simple and efficient method for synthesizing 2-(pyrrol-3-yl)benzimidazoles},
journal = {Russian Chemical Bulletin},
year = {2011},
volume = {60},
publisher = {Springer Nature},
month = {feb},
url = {https://doi.org/10.1007/s11172-011-0059-1},
number = {2},
pages = {368--372},
doi = {10.1007/s11172-011-0059-1}
}
Cite this
MLA
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Mamedov, V. A., et al. “Benzimidazoles and related heterocycles 10. A novel acid-catalyzed rearrangement in the system 3-(α-aminobenzyl)quinoxalin-2(1H)-one-ethyl acetoacetate as a simple and efficient method for synthesizing 2-(pyrrol-3-yl)benzimidazoles.” Russian Chemical Bulletin, vol. 60, no. 2, Feb. 2011, pp. 368-372. https://doi.org/10.1007/s11172-011-0059-1.