Abstract
Condensation of 2-amino-3-hydroxypyridine with thenoyl chloride in 1-methyl-2-pyrrolidon afforded 2-(2-thienyl)oxazolo[4,5-b]pyridine. Reactivity of the latter towards electrophilic substitution (nitration, bromination, formylation, acylation) was studied. It is shown that the reaction occurred exclusively at the position 5 of the thiophene ring. Nucleophilic substitution of pyridine ring was performed. Quaternization of 2-(2-thienyl)oxazolo[4,5-b]pyridine with methyl iodide in benzene was carried out. Chichibabin amination with an excess of sodium amide in xylene failed.
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Original Russian Text © A.A. Aleksandrov, M.M. El’chaninov, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 4, pp. 614–617.
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Aleksandrov, A.A., El’chaninov, M.M. Synthesis and reactivity of 2-(2-thienyl)oxazolo[4,5-b]pyridine. Russ J Gen Chem 85, 858–860 (2015). https://doi.org/10.1134/S1070363215040155
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DOI: https://doi.org/10.1134/S1070363215040155