Domino Aza-Annulations of Enynyl-/(Alkynyl)aryl-acetonitriles to Access Nitrogen-Enriched Heterocycles.
J Org Chem
; 87(17): 11547-11557, 2022 Sep 02.
Article
em En
| MEDLINE
| ID: mdl-35998892
ABSTRACT
Unprecedented domino aza-annulations of (E)-2-en-4-ynyl-acetonitriles (generated from the Morita-Baylis-Hillman acetates of propiolaldehydes for the first time) with sodium azide under metal- and oxidant-free conditions for the assembly of triazolo-pyridines are accomplished. The developed strategy offers broad substrate scope, extending to (2-alkynyl)aryl and indolyl-acetonitriles to provide the corresponding triazolo-fused isoquinolines and ß-carbolines, respectively, in good yields. Additionally, the synthetic utility of the products is demonstrated via denitrogenative coupling of fused triazoles with different nucleophiles.
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MEDLINE
Idioma:
En
Ano de publicação:
2022
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Article