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Tandem Aza Michael Addition–Vinylogous Nitroaldol Condensation: Construction of Highly Substituted N-Fused 3-Nitropyrazolopyridines

Author:
Obulesu, Owk, Murugesh, V., Harish, Battu, Suresh, Surisetti
Source:
Journal of organic chemistry 2018 v.83 no.12 pp. 6454-6465
ISSN:
1520-6904
Subject:
aldehydes, chemical reactions, chemical structure, ketones, organic chemistry
Abstract:
A base-mediated tandem aza-Michael addition–vinylogous nitroaldol condensation has been described between 3,5-dialkyl 4-nitropyrazoles and alkynyl ketones/aldehydes. This transition metal-free atom economical transformation occurred via C–N and C═C bond formations in one step with the elimination of water. The construction of a variety of highly substituted N-fused 3-nitropyrazolopyridine derivatives has been demonstrated with good yields. Good to excellent regioselectivities have been achieved with unsymmetrically substituted 4-nitropyrazoles.
Agid:
6047294