76681-89-5Relevant academic research and scientific papers
A Novel Oxamide Rearrangement
Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.
, p. 1513 - 1518 (2007/10/02)
An efficient, base-induced rearrangement of 2-benzoic acid methyl ester (7a) to the isomeric 2-benzoic acid methyl ester (27a) is described.This novel rearrangement must proceed through a spiro intermediate wherein benzoate is acting as a Michael receptor.When 2-benzoic acid methyl ester (28) - an oxamide which would produce a degenerate spiro intermediate - was subjected to rearrangement conditions, the product obtained was 1,3-dimethyl-2,4-(1H,3H)quinazolinedione (29).This latter transformation may have proceeded via a benzodiazepinetrione intermediate.
