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- Title
Synthesis of functionally substituted isoxazole and isothiazole derivatives.
- Authors
Potkin, V. I.; Petkevich, S. K.; Kletskov, A. V.; Dikusar, E. A.; Zubenko, Yu. S.; Zhukovskaya, N. A.; Kazbanov, V. V.; Pashkevich, S. G.
- Abstract
Acylation of benzene and toluene with 5-phenyl- and 5-( p-tolyl)isoxazole-3-carbonyl chlorides gave 5-phenyl(or p-tolyl)isoxazol-3-yl phenyl(or p-tolyl)ketones which were reduced to the corresponding alcohols with sodium tetrahydridoborate in propan-2-ol. Selective reduction of the carboxy group in 4,5-dichloroisothiazole-3-carboxylic acid was achieved by the action of BH 3, and the aldehyde group in 4-formyl-2-methoxyphenyl 5-arylisoxazole-3-carboxylates and 4,5-dichloroisothiazole-3-carboxylates was reduced to hydroxymethyl group with sodium triacetoxyhydridoborate in benzene. Acylation of the resulting hydroxymethyl derivatives with 5-arylisoxazole- and 4,5-dichloroisothiazole-3-carbonyl chlorides afforded the corresponding esters containing two azole fragments in their molecules.
- Subjects
ISOXAZOLES; CHEMICAL synthesis; ISOTHIAZOLE; CHEMICAL derivatives; ACYLATION; BENZENE; CARBOXYLATES
- Publication
Russian Journal of Organic Chemistry, 2013, Vol 49, Issue 10, p1523
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428013100205