Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc
Publication type: Journal Article
Publication date: 2021-08-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
2- and 4-(Arylmethylideneamino)phenols react with Reformatsky reagent, obtained from methyl 1-bromocyclohexanecarboxylate and zinc, to form 3-aryl-2-[2-(or 4-)hydroxyphenyl]-2-azaspiro[3.5]nonan-1-ones. The reaction involves the initial addition of the organozinc reagent across the C=N double bond of the Schiff base and the subsequent intramolecular cyclization of the adduct via the nucleophilic attack of the nitrogen atom on the ester carbonyl carbon atom. The structures of the products were confirmed by X-ray diffraction analysis.
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Nikiforova E. M. et al. Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc // Russian Journal of Organic Chemistry. 2021. Vol. 57. No. 8. pp. 1275-1280.
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Nikiforova E. M., Baibarodskikh D. V., Zverev D. P., Dmitriev M. V., Kirillov N. F. Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc // Russian Journal of Organic Chemistry. 2021. Vol. 57. No. 8. pp. 1275-1280.
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TY - JOUR
DO - 10.1134/S1070428021080066
UR - https://link.springer.com/10.1134/S1070428021080066
TI - Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc
T2 - Russian Journal of Organic Chemistry
AU - Nikiforova, Elena M.
AU - Baibarodskikh, D V
AU - Zverev, D P
AU - Dmitriev, Maksim V
AU - Kirillov, N F
PY - 2021
DA - 2021/08/01
PB - Pleiades Publishing
SP - 1275-1280
IS - 8
VL - 57
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2021_Nikiforova,
author = {Elena M. Nikiforova and D V Baibarodskikh and D P Zverev and Maksim V Dmitriev and N F Kirillov},
title = {Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc},
journal = {Russian Journal of Organic Chemistry},
year = {2021},
volume = {57},
publisher = {Pleiades Publishing},
month = {aug},
url = {https://link.springer.com/10.1134/S1070428021080066},
number = {8},
pages = {1275--1280},
doi = {10.1134/S1070428021080066}
}
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Nikiforova, Elena M., et al. “Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc.” Russian Journal of Organic Chemistry, vol. 57, no. 8, Aug. 2021, pp. 1275-1280. https://link.springer.com/10.1134/S1070428021080066.