Tandem Ring‐Opening/Double Ring‐Closing Synthesis of 1,2,4‐Triazolo[1,5‐a]pyridines from Chromone‐Containing Acrylonitriles

Author:

Chernov Nikita M.1ORCID,Kustin Roman P.1,Pypa Yulia V.1,Anisimov Sergej O.1,Spiridonova Dar'ya V.2,Shutov Roman V.1,Yakovlev Igor P.1

Affiliation:

1. Department of Organic Chemistry Saint-Petersburg State Chemical and Pharmaceutical University Prof. Popov st., 14 Saint-Petersburg 197376 Russia

2. Research Park St. Petersburg State University Universitetskaya emb., 7–9 Saint-Petersburg 199034 Russia

Abstract

AbstractWe studied a reaction of chromone‐containing acrylonitriles and cyanoacrylates with acid hydrazides. This reaction turned out to be a method for the synthesis of salicyloyl‐substituted 1,2,4‐triazolo[1,5‐a]pyridines. The synthesis developed is a tandem ring‐opening/double ring‐closing process. This synthetic approach is characterized by low toxic solvents (ethanol, butanol) and mediator (Et3N), 37–84% yields, non‐chromatographic isolation of products, and substrate tolerance (59 examples).

Funder

Ministry of Health of the Russian Federation

Publisher

Wiley

Subject

General Chemistry

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