Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Regular Article
Long-Range Halogen Dance Reaction in 4,5-Dihalogeno-2-(Sulfur-Containing Heterocyclyl)thiazole
Yoshimi HirokawaKenji ArimitsuYuriko IkegawaTaiga KashiharaMizuki KosudaAiri MiuraNaoyoshi Maezaki
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Supplementary material

2024 Volume 72 Issue 12 Pages 1061-1064

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Abstract

We have investigated the base-induced long-range halogen dance reactions of 4,5-dibromo- or 4-bromo-5-iodothiazoles bearing sulfur-containing aromatic heterocycles at the C2-position. We have found that the reaction occurs in bithiazole regioisomers or (thiophenyl)thiazole derivatives, in which the C-5 halo group on the thiazole halogen donor regioselectively migrates to a halogen acceptor ring after treatment with lithium bis(trimethylsilyl)amide. The substrate with a thiophen-2-yl substituent required highly basic P4-t-Bu to induce the halogen dance reaction.

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Published by The Pharmaceutical Society of Japan

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