Tandem Ring-Opening/Double Ring-Closing Synthesis of 1,2,4-Triazolo[1,5-a]pyridines from Chromone-Containing Acrylonitriles |
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| Authors: | Nikita M. Chernov Roman P. Kustin Yulia V. Pypa Sergej O. Anisimov Dar'ya V. Spiridonova Roman V. Shutov Igor P. Yakovlev |
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| 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 |
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| Abstract: | We 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). |
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| Keywords: | amphiphiles cyclization chromones heterocycles hydrazides nucleophilic addition |
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