Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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An Efficient Synthesis of New Pyrazolines and Isoxazolines Bearing Thiazolyl and Etheral Pharmacophores

  • Bhosle, Manisha R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mali, Jyotirling R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Pratap, Umesh R. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University) ;
  • Mane, Ramrao A. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
  • Received : 2012.02.13
  • Accepted : 2012.03.24
  • Published : 2012.06.20
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Abstract

A convenient synthetic route has been developed to synthesize 5-(4-((2-phenylthiazol-4-yl) methoxy)phenyl)-3-(4-sustituted phenyl)pyrazolines (5a-f) and 5-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-3-(4-substituted phenyl)isoxazolines (6a-f) starting from 2-phenyl-4-chloromethylthiazole (1). The chloromethylthiazole (1) was first condensed with 4-hydroxy benzaldehyde (2) for obtaining 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3). Claisen-Smidth condensation of 4-((2-phenylthiazol-4-yl)methoxy)benzaldehyde (3) and acetophenones has been carried in alkaline alcohol and obtained 3-(4-((2-phenylthiazol-4-yl)methoxy)phenyl)-1-(4-substituted phenyl)prop-2-en-1-ones (4a-f). The cyclocondensation of 2-propen-1-ones has been first time carried separately with hydrazine hydrate and hydroxylamine hydrochloride in aqueous micellar tetradecyltrimethylammonium bromide (TTAB) medium for getting the titled heterocycles with good to excellent yields.

Keywords

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