One-pot domino synthesis of five- and six-membered fused dihydropyridines promoted by PPh 3 -NBS in aqueous medium

A facile one-pot synthesis of five- and six-membered fused dihydropyridines such as chromenodihydropyridines, pyrazolodihydropyridines and isoxazolopyridines was accomplished for the first time by employing PPh -NBS a formal [3 + 2 + 1] cycloaddition of 1,3-bisnucleophiles ( , 2-aminochromone, 4-ami...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-05, Vol.21 (21), p.4434-4439
Main Authors: Banda, Bhanu Prasad, Medishetti, Nagaraju, Nanubolu, Jagadeesh Babu, Atmakur, Krishnaiah
Format: Article
Language:English
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Summary:A facile one-pot synthesis of five- and six-membered fused dihydropyridines such as chromenodihydropyridines, pyrazolodihydropyridines and isoxazolopyridines was accomplished for the first time by employing PPh -NBS a formal [3 + 2 + 1] cycloaddition of 1,3-bisnucleophiles ( , 2-aminochromone, 4-aminochromone, 5-aminopyrazole and 5-aminoisoxazole), β-enaminones and aldehydes in aqueous medium. The present approach involves a Michael type addition followed by intramolecular cyclization leading to the formation of two new C-C bonds and one C-N bond. High compatibility and excellent yields are the advantages of this protocol.
ISSN:1477-0520
1477-0539
DOI:10.1039/D3OB00472D