Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles
Publication type: Journal Article
Publication date: 2017-08-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
Reaction of enaminoesters, derivatives of 2,2-dialkyl-1,2,3,4-tetrahydrobenzo[f]isoquinoline, with oxalyl chloride leads to the formation of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]-isoquinoline-10-carboxylates. At reaction of the latter with ammonia and cyclic amines opening of pyrroledione cycle occurs and the formation of enaminoketoamides, and the reaction with o-phenylenediamine furnishes a fragment of benzimidazole. Hydroxylamine behaves as binucleophile and attacks not only lactam, but also the ester group, affording heterocyclic system of isoxazine-3,4,6-trione.
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Mikhailovskii А. G., Yusov А. S., Gashkova О. V. Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles // Russian Journal of Organic Chemistry. 2017. Vol. 53. No. 8. pp. 1222-1225.
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Mikhailovskii А. G., Yusov А. S., Gashkova О. V. Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles // Russian Journal of Organic Chemistry. 2017. Vol. 53. No. 8. pp. 1222-1225.
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TY - JOUR
DO - 10.1134/s1070428017080103
UR - https://doi.org/10.1134/s1070428017080103
TI - Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles
T2 - Russian Journal of Organic Chemistry
AU - Mikhailovskii, А G
AU - Yusov, А S
AU - Gashkova, О V
PY - 2017
DA - 2017/08/01
PB - Pleiades Publishing
SP - 1222-1225
IS - 8
VL - 53
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2017_Mikhailovskii,
author = {А G Mikhailovskii and А S Yusov and О V Gashkova},
title = {Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles},
journal = {Russian Journal of Organic Chemistry},
year = {2017},
volume = {53},
publisher = {Pleiades Publishing},
month = {aug},
url = {https://doi.org/10.1134/s1070428017080103},
number = {8},
pages = {1222--1225},
doi = {10.1134/s1070428017080103}
}
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MLA
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Mikhailovskii, А. G., et al. “Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles.” Russian Journal of Organic Chemistry, vol. 53, no. 8, Aug. 2017, pp. 1222-1225. https://doi.org/10.1134/s1070428017080103.