HTIB-Mediated One-Pot Synthesis of Some 2-Substituted 4-Styrylthiazoles from (E)-4-Arylbut-3-en-2-ones

Abstract

The reaction of (E)-4-arylbut-3-en-2-ones with [(hydroxy(tosyloxy)iodo]benzene (HTIB) followed by treatment with thioureas, thioamide, and thiobenzamide has offered a one-pot synthesis of 2-substituted 4-styrylthiazoles.

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GRAPHICAL ABSTRACT

Keywords:

• (E)-4-Arylbut-3-en-2-ones
• (E)-4-aryl-1-tosyloxy-but-3-en-2-ones; α-haloketones
• [hydroxy(tosyloxy)iodo]benzene
• 4-styrylthiazoles
• α-tosyloxyketones

ACKNOWLEDGMENT

We are thankful to Kurukshetra University, Kurukshetra, India, for the award of a university research scholarship to Nitya Sharma and to the Council of Scientific and Industrial Research, New Delhi, India, for the award of a senior research fellowship to Pooja Ranjan for carrying out this work. The authors are also thankful to the Council of Scientific and Industrial Research (CSIR 01(2186)/07/EMR-II) for financial support.

Notes

^a Yields of products 4 with regard to 2.

^b Yields of products 4 with regard to 1.

^c Lit mp°C (4a 160–162, 4g 83, and 4k 177–180).

^d Yield of product (4a 49%, 4g 64%, and 4k 19%) with regard to iodomethylstyrylketone. To compare the results of present study with literature procedure, we carried out the synthesis of p-methylliodobenzalacetone according to Ref. 6, which on treatment with thioacetamide resulted in the formation of 4l. However, overall yield of the product 4l was only 10% against 83% obtained from the present study.