2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides
2
Chuvash State Agricultural Academy, Cheboksary, Russia
|
Publication type: Journal Article
Publication date: 2014-08-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Reactions of 2-aroyl-1,1,3,3-tetracyanopropenides with hydrogen halides in solvents of low dielectric permittivity result in the formation of 6-amino-2-aroyl-2-halopyridine-3,5-dicarbonitriles. 2-Acyl-1,1,3,3-tetracyanopropenides under similar conditions afford 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles. In solvents of high dielectric permittivity the result of the reaction depends on the nature of the hydrogen halide and the acyl(aroyl) substituent: With HCl and HBr 2-aroyl-1,1,3,3-tetracyanopropenides form 2-(5-amino-2-aryl-2-halo-4-cyano-2,3-dihydrofuran-3-ylidene)-propanedinitriles, and 2-acyl-1,1,3,3-tetracyanopropenides give 2-(2-alkylidene-5-amino-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles; with HI depending on the reaction conditions and the structure of the acyl substituent 2-(5-amino-2-aryl-4-cyano-2,3-dihydrofuran-3-ylidene)propanedinitriles, 2-(5-amino-4-cyano-2,3-dihydrofuran-3-ylidene) propane-dinitrile, 2-amino-4-(dimethoxybenzyl)-6-iodo-5-cyanonicotinamide, 4-amino-6-iodo-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile, or 4-amino-6-iodo-3-oxo-1-ethylidene-1,3-dihydrofuro[3,4-c]pyridine-7-carbonitrile are obtained.
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Kayukov Ya. S. et al. 2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides // Russian Journal of Organic Chemistry. 2014. Vol. 50. No. 8. pp. 1097-1106.
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Kayukov Ya. S., Karpov S. V., Kayukova O. V., Ershov O. V., Nasakin O. E. 2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides // Russian Journal of Organic Chemistry. 2014. Vol. 50. No. 8. pp. 1097-1106.
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RIS
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TY - JOUR
DO - 10.1134/s1070428014080053
UR - https://doi.org/10.1134/s1070428014080053
TI - 2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides
T2 - Russian Journal of Organic Chemistry
AU - Kayukov, Ya S
AU - Karpov, S. V.
AU - Kayukova, O V
AU - Ershov, O V
AU - Nasakin, O E
PY - 2014
DA - 2014/08/01
PB - Pleiades Publishing
SP - 1097-1106
IS - 8
VL - 50
SN - 1070-4280
SN - 1608-3393
ER -
Cite this
BibTex (up to 50 authors)
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@article{2014_Kayukov,
author = {Ya S Kayukov and S. V. Karpov and O V Kayukova and O V Ershov and O E Nasakin},
title = {2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides},
journal = {Russian Journal of Organic Chemistry},
year = {2014},
volume = {50},
publisher = {Pleiades Publishing},
month = {aug},
url = {https://doi.org/10.1134/s1070428014080053},
number = {8},
pages = {1097--1106},
doi = {10.1134/s1070428014080053}
}
Cite this
MLA
Copy
Kayukov, Ya. S., et al. “2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides: VI. Reaction with hydrogen halides.” Russian Journal of Organic Chemistry, vol. 50, no. 8, Aug. 2014, pp. 1097-1106. https://doi.org/10.1134/s1070428014080053.