Pleiades Publishing
Russian Journal of Organic Chemistry
,  volume 56 ,  issue 7 ,  pages 1187-1190

Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles

Ya S Kayukov 1
, 
A A Grigorev 1
, 
S. V. Karpov 1
, 
O V Kayukova 2
, 
A.A. Mikhaylov 3
1
 
I.N. Ul’yanov Chuvashskii State University, Cheboksary, Russia | 
2
 
Chuvash State Agricultural Academy, Cheboksary, Russia | 
3
 
Publication type: Journal Article
Publication date: 2020-07-01
Pleiades Publishing
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Base-catalyzed reaction of 3-aroyl-6-halopyridine-3,5-dicarbonitriles with alcohols involved successive regioselective pyrrole ring fusion at the pyridine [c] side and nucleophilic substitution of chlorine. Pyrrole ring closure is the result of initial formation of furan ring with participation of the carbonyl and cyano groups, followed by iminolactone–lactam rearrangement. The reaction in anhydrous alcohol afforded 1,6-dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles. If water was present in the alcohols, the products were 6-alkoxy-4-amino-1-aryl-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles.
Found 

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Kayukov Ya. S. et al. Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles // Russian Journal of Organic Chemistry. 2020. Vol. 56. No. 7. pp. 1187-1190.
GOST all authors (up to 50) Copy
Kayukov Ya. S., Grigorev A. A., Karpov S. V., Kayukova O. V., Mikhaylov A. Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles // Russian Journal of Organic Chemistry. 2020. Vol. 56. No. 7. pp. 1187-1190.
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RIS Copy
TY - JOUR
DO - 10.1134/S1070428020070106
UR - https://doi.org/10.1134/S1070428020070106
TI - Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles
T2 - Russian Journal of Organic Chemistry
AU - Kayukov, Ya S
AU - Grigorev, A A
AU - Karpov, S. V.
AU - Kayukova, O V
AU - Mikhaylov, A.A.
PY - 2020
DA - 2020/07/01
PB - Pleiades Publishing
SP - 1187-1190
IS - 7
VL - 56
SN - 1070-4280
SN - 1608-3393
ER -
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BibTex (up to 50 authors) Copy
@article{2020_Kayukov,
author = {Ya S Kayukov and A A Grigorev and S. V. Karpov and O V Kayukova and A.A. Mikhaylov},
title = {Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles},
journal = {Russian Journal of Organic Chemistry},
year = {2020},
volume = {56},
publisher = {Pleiades Publishing},
month = {jul},
url = {https://doi.org/10.1134/S1070428020070106},
number = {7},
pages = {1187--1190},
doi = {10.1134/S1070428020070106}
}
MLA
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MLA Copy
Kayukov, Ya. S., et al. “Synthesis of 6-Alkoxy- and 1,6-Dialkoxy-4-amino-1-aryl-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles.” Russian Journal of Organic Chemistry, vol. 56, no. 7, Jul. 2020, pp. 1187-1190. https://doi.org/10.1134/S1070428020070106.