Intramolecular 6-endo-dig-Cyclization of Ethyl 5-Aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate
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The reaction of 5-aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylic acid ethyl ester with bases has given ethyl 5-sulfanylidene-4,5,6,7-tetrahydrofuro[2,3-c]pyridine-2-carboxylate as a result of intramolecular 6-endo-dig-cyclization of thioketene generated in situ with an internal CH2NH2 nucleophile. The obtained ester has been alkylated with iodomethane at the sulfur atom to form ethyl 5-methylsulfanyl-4,7-dihydrofuro[2,3-c] pyridine-2-carboxylate. The Hantzsch reaction with ω-bromoacetophenone has resulted in the formation of 7-ethoxycarbonyl-3-phenylfuro[3,2-d[1,3]thiazolo[3,2-a]pyridin-4-ium bromide.
Keywords1,2,3-thiadiazoles 4-(furan-3-yl)-1,2,3-thiadiazoles furo[2,3-c]pyridines 1,3-thiazolium salts 1,3-thiazolo[3,2-a]pyridines
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This study was carried out in the scope of the basic part of state project of Ministry of Education and Science of Russian Federation (project no. 4.5554.2017/8.9) using the equipment of the Engineering Center of St. Petersburg State Institute of Technology (Technical University).
Conflict of Interest
No conflict of interest was declared by the authors.