Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

HEREDIA MOYA, JORGE HUMBERTO; Daniel A. Zurita; José Eduardo Cadena-Cruz; Christian D. Alcívar-León

doi:10.3390/molecules27196708

Diaza-1,3-butadienes as Useful Intermediate in Heterocycles Synthesis

Journal

Molecules

ISSN

1420-3049

Date Issued

2022-10-09

Author(s)

HEREDIA MOYA, JORGE HUMBERTO

Facultad de Ciencias de la Salud Eugenio Espejo

Daniel A. Zurita

José Eduardo Cadena-Cruz

Christian D. Alcívar-León

DOI

10.3390/molecules27196708

URL

https://cris.ute.edu.ec/handle/123456789/482

Abstract

Many heterocyclic compounds can be synthetized using diaza-1,3-butadienes (DADs) as key structural precursors. Isolated and in situ diaza-1,3-butadienes, produced from their respective precursors (typically imines and hydrazones) under a variety of conditions, can both react with a wide range of substrates in many kinds of reactions. Most of these reactions discussed here include nucleophilic additions, Michael-type reactions, cycloadditions, Diels–Alder, inverse electron demand Diels–Alder, and aza-Diels–Alder reactions. This review focuses on the reports during the last 10 years employing 1,2-diaza-, 1,3-diaza-, 2,3-diaza-, and 1,4-diaza-1,3-butadienes as intermediates to synthesize heterocycles such as indole, pyrazole, 1,2,3-triazole, imidazoline, pyrimidinone, pyrazoline, -lactam, and imidazolidine, among others. Fused heterocycles, such as quinazoline, isoquinoline, and dihydroquinoxaline derivatives, are also included in the review.