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Selective Synthesis of 3‐(α,α‐Dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one as an Excellent Precursor for the Synthesis of 2‐Substituted 4‐(4‐Hydroxy‐6‐methyl‐2 H ‐2‐oxopyran‐3‐yl)thiazoles as Antimicrobial and Antifungal Agents
Author(s) -
Kapoor Jitander K.,
Prakash Richa,
Kumar Ajay,
Saini Deepika,
Arora Loveena
Publication year - 2018
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3116
Subject(s) - chemistry , pyran , halogenation , antifungal , antimicrobial , stereochemistry , organic chemistry , medicine , dermatology
A selective synthesis of 3‐(α,α‐dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2 H ‐pyran‐2‐one ( 3 ) has been achieved by bromination of DHA using CuBr 2 /CHCl 3 ‐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‐2 H ‐2‐oxopyran‐3‐yl)thiazoles. These thiazoles were evaluated for their antimicrobial and antifungal activity.