Synthesis of 1,3-benzothiazol-2(3H)-one and some its derivatives

Autor:	O. L. Titova, E. A. Melent’eva, A. K. Kuanchalieva, A. V. Velikorodov
Rok vydání:	2011
Předmět:	Acylation chemistry.chemical_compound Allyl bromide chemistry Methyl chloroformate Organic Chemistry Pyridine Regioselectivity Organic chemistry Alkylation Chloroacetyl chloride Triethylamine
Zdroj:	Russian Journal of Organic Chemistry. 47:1375-1379
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s107042801109020x
Popis:	Acylation of 2-aminobenzenethiol with methyl chloroformate in pyridine gave dimethyl 2,2′-disulfanediylbis(2,1-phenylene)dicarbamate instead of expected methyl 2-suylfanylphenylcarbamate. Heating of the product with zinc dust in glacial acetic acid led to the formation of 1,3-benzothiazol-2(3H)-one. Alkylation of the latter with 1,2-dibromoethane and allyl bromide, as well as acylation with chloroacetyl chloride, afforded the corresponding 3-substituted derivatives. 3-[3-(Pyridin-2-yl)-4,5-dihydroisoxazol-5-ylmethyl]-1,3-benzothiazol-2(3H)-one was synthesized with high regioselectivity by 1,3-dipolar cycloaddition of 3-allyl-1,3-benzothiazol-2(3H)-one to pyridine-2-carbonitrile oxide generated fromN-hydroxypyridine-2-carboximidoyl chloride hydrochloride by the action of triethylamine.
Databáze:	OpenAIRE
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