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

Makoto Ueno; Hideo Togo

doi:10.1055/s-2004-831242

PAPER

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

Makoto Ueno^a, 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;

Abstract

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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

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

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