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
1
I.N. Ul’yanov Chuvashskii State University, Cheboksary, Russia
|
2
Chuvash State Agricultural Academy, Cheboksary, Russia
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Publication type: Journal Article
Publication date: 2020-07-01
Journal:
Russian Journal of Organic Chemistry
Quartile SCImago
Q4
Quartile WOS
Q4
Impact factor: 0.8
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.
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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.
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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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TY - JOUR
DO - 10.1134/S1070428020070106
UR - https://doi.org/10.1134%2FS1070428020070106
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 - Kayukova, O V
AU - Mikhaylov, A.A.
AU - Karpov, S. V.
PY - 2020
DA - 2020/07/01 00:00:00
PB - Pleiades Publishing
SP - 1187-1190
IS - 7
VL - 56
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2020_Kayukov
author = {Ya S Kayukov and A A Grigorev and O V Kayukova and A.A. Mikhaylov and S. V. Karpov},
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%2FS1070428020070106},
number = {7},
pages = {1187--1190},
doi = {10.1134/S1070428020070106}
}
Cite this
MLA
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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, vol. 56, no. 7, Jul. 2020, pp. 1187-1190. https://doi.org/10.1134%2FS1070428020070106.
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