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Synthesis 2004(16): 2673-2677  
DOI: 10.1055/s-2004-831242
PAPER
© Georg Thieme Verlag Stuttgart · New York

Environmentally Benign Preparation of Heteroaromatics from Ketones or Alcohols, with Macroporous Polystyrenesulfonic Acid and (Diacetoxy­iodo)benzene, Followed by Thioamide, Amidine, and 2-Aminopyridine

Makoto Uenoa, Hideo Togo*a,b
a Graduate School of Science and Technology, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
b Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
e-Mail: togo@faculty.chiba-u.jp;
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Publication History

Received 2 June 2004
Publication Date:
22 September 2004 (online)

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Abstract

An operationally simple, efficient, and environmentally benign preparation of heteroaromatics such as thiazoles, imidazoles, and imidazo[1,2-a]pyridines from the reactions of a polymer-supported [hydroxy(sulfonyloxy)iodo]benzene (2) with ketones or alcohols, followed by treatment with thioamides, benzamidine, and 2-aminopyridine, respectively, in the presence of potassium carbonate were successfully carried out.

Key Words

heterocycles - alcohols - ketones - thiazole - imidazole - pyridines