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- Title
Synthesis of 1,3-benzothiazol-2(3 H)-one and some its derivatives.
- Authors
Velikorodov, A.; Kuanchalieva, A.; Melent'eva, E.; Titova, O.
- Abstract
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(3 H)-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(3 H)-one was synthesized with high regioselectivity by 1,3-dipolar cycloaddition of 3-allyl-1,3-benzothiazol-2(3 H)-one to pyridine-2-carbonitrile oxide generated from N-hydroxypyridine-2-carboximidoyl chloride hydrochloride by the action of triethylamine.
- Subjects
BIOSYNTHESIS; PYRIDINE; ZINC powder; ACETIC acid; ALKYLATION; ETHYLENE dibromide; ACYLATION
- Publication
Russian Journal of Organic Chemistry, 2011, Vol 47, Issue 9, p1375
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S107042801109020X