Novel oxidative alpha-tosyloxylation of alcohols with iodosylbenzene and p-toluenesulfonic acid and its synthetic use for direct preparation of heteroaromatics

Makoto Ueno; Takahiro Nabana; Hideo Togo

doi:10.1021/jo030045t

Novel oxidative alpha-tosyloxylation of alcohols with iodosylbenzene and p-toluenesulfonic acid and its synthetic use for direct preparation of heteroaromatics

J Org Chem. 2003 Aug 8;68(16):6424-6. doi: 10.1021/jo030045t.

Authors

Makoto Ueno¹, Takahiro Nabana, Hideo Togo

Affiliation

¹ Graduate School of Science and Technology, and Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522 Japan.

PMID: 12895080
DOI: 10.1021/jo030045t

Abstract

alpha-Tosyloxyketones and alpha-tosyloxyaldehydes were directly prepared from alcohols by treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate in good yields. This method can be used for the direct preparation of thiazoles, imidazoles, and imidazo[1,2-a]pyridines from alcohols in good to moderate yields by the successive treatment with iodosylbenzene and p-toluenesulfonic acid monohydrate, followed by thioamides, benzamidine, and 2-aminopyridine, respectively.