Russian Journal of Organic Chemistry

, Volume 49, Issue 10, pp 1523–1533 | Cite as

Synthesis of functionally substituted isoxazole and isothiazole derivatives

  • V. I. Potkin
  • S. K. Petkevich
  • A. V. Kletskov
  • E. A. Dikusar
  • Yu. S. Zubenko
  • N. A. Zhukovskaya
  • V. V. Kazbanov
  • S. G. Pashkevich
Article

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 BH3, 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.

Keywords

Thionyl Chloride Methanone Isothiazole Isoxazole Derivative Sodium Tetrahydridoborate 

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Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • V. I. Potkin
    • 1
  • S. K. Petkevich
    • 1
  • A. V. Kletskov
    • 1
  • E. A. Dikusar
    • 1
  • Yu. S. Zubenko
    • 1
  • N. A. Zhukovskaya
    • 1
  • V. V. Kazbanov
    • 2
  • S. G. Pashkevich
    • 2
  1. 1.Institute of Physical Organic ChemistryNational Academy of Sciences of BelarusMinskBelarus
  2. 2.Institute of PhysiologyNational Academy of Sciences of BelarusMinskBelarus

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