Intramolecular 6-endo-dig-Cyclization of Ethyl 5-Aminomethyl-4-(1,2,3-thiadiazol-4-yl)furan-2-carboxylate
- Authors: Remizov Y.O.1, Pevzner L.M.1, Petrov M.L.1
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Affiliations:
- St. Petersburg State Institute of Technology
- Issue: Vol 89, No 10 (2019)
- Pages: 2151-2153
- Section: Letters to the Editor
- URL: https://journals.rcsi.science/1070-3632/article/view/223137
- DOI: https://doi.org/10.1134/S1070363219100268
- ID: 223137
Cite item
Abstract
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.
About the authors
Yu. O. Remizov
St. Petersburg State Institute of Technology
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
L. M. Pevzner
St. Petersburg State Institute of Technology
Author for correspondence.
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013
M. L. Petrov
St. Petersburg State Institute of Technology
Email: pevzner_lm@list.ru
Russian Federation, Moskovskii pr. 26, St. Petersburg, 190013