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The Vilsmeier cyclization of azides. Synthesis of oxazoles and vinyl azides from 2-azidoacetophenones

โœ Scribed by Vattoly J. Majo; Paramasivan T. Perumal

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
218 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The synthesis of 5-aryloxazole-4-carbexaldebydes was accomplished by an unprecedented Vflsmeier cyclization of 2-azidoacetophenones. One-pot synthesis of these oxazolecarboxaldehydes from 2-bromoacetopbenones by dehaloazidation-Vilsmeier cyclization reaction sequence provided better yields. The treatment of 2-azidoacetopbenones with Vilsmeier reagent (DMF/I'OCi3) at rt resulted in the exclusive formation of ct-azido-I~-chlorovinyl azides in moderate yields.

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