An Investigation of the Scope and Limitations of the Cornforth Rearrangement.

摘要

The Cornforth rearrangement of 5-ethoxyoxazole-4-carboxamides has been used to prepare ethyl 5-aminooxazole-4-carboxylates. P-Tolyl-2-phenyl-5-methoxyoxazole-4-thiocarboxylate rearranged similarly to give methyl 2-phenyl-5-p-tolylthiooxazole-4-carboxylate. 2-Phenyl-5-ethoxyoxazole-4-carboxylic acid fluoride and ethyl Beta-(2-Phenyl-5-chlorooxazole-4) acrylate failed to rearrange on thermolysis. When the 4-carbonyl functionality of the oxazole ring was replaced by an imino group, rearrangement took place leading to the imidazole derivative. (Author)