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Long-Range Halogen Dance Reaction in 4,5-Dihalogeno-2-(Sulfur-Containing Heterocyclyl)thiazole
Yoshimi Hirokawa1, Kenji Arimitsu1, Yuriko Ikegawa1
1Faculty of Pharmacy, Osaka Ohtani University.
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 P
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