4.4 Article

Selective Synthesis of 3-(α,α-Dibromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one as an Excellent Precursor for the Synthesis of 2-Substituted 4-(4-Hydroxy-6-methyl-2H-2-oxopyran-3-yl)thiazoles as Antimicrobial and Antifungal Agents

Journal

JOURNAL OF HETEROCYCLIC CHEMISTRY
Volume 55, Issue 4, Pages 899-906

Publisher

WILEY
DOI: 10.1002/jhet.3116

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A selective synthesis of 3-(alpha alpha-dibromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (3) has been achieved by bromination of DHA using CuBr2/CHCl3-EtOAc. The reaction of 3 with different thioureas/ thiomides/ thiosemicarbazide offers a convenient and efficient method for the syntheses of 2-substituted 4-(4-hydroxy-6-methyl-2H-2-oxopyran-3-yl) thiazoles. These thiazoles were evaluated for their antimicrobial and antifungal activity.

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