Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 17, Pages 11547-11557Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01136
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- University Grants Commission, New Delhi
- Science and Engineering Research Board (SERB), New Delhi [EMR/2016/006253]
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Unprecedented domino aza-annulations of (E)-2-en-4-ynyl-acetonitriles with sodium azide under metal-and oxidant-free conditions for the assembly of triazolo-pyridines are accomplished. The developed strategy offers broad substrate scope and demonstrated its synthetic utility via denitrogenative coupling of fused triazoles with different nucleophiles.
Unprecedented domino aza-annulations of (E)-2-en-4-ynyl-acetonitriles (generated from the Morita-Baylis-Hill-man 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 isoquino-lines and beta-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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