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Ring Transformations of Thiazoles into Imidazoles

✍ Scribed by Gerrit L'Abbé; Wim Meutermans; Maria Bruynseels

Publisher
Wiley (John Wiley & Sons)
Year
2010
Weight
95 KB
Volume
95
Category
Article
ISSN
0037-9646

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✦ Synopsis

In one of the rare published examples on the title reaction, Cook and coworkers' reported on the Dimroth rearrangement2 of the 5-aminothiazole 1 to the dithiohydantoin 2 followed by mild oxidation to an orange product (mp 270") having structure 2. We have re-examined this reaction and have come to different conclusions about the structures of starting and final products.

Compound 1 (mp 263O), prepared in 73% yield by heating a-aminobenzyl cyanide

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