P. PeetNorton, S. Sunder, R. Barbuch
Nov 1, 1980
Citations
0
Influential Citations
6
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
An efficient, base-induced rearrangement of 2-[(1,2-dioxo-2-(methylamino)ethyl)phenylamino]benzoic acid methyl ester (7a) to the isomeric 2-[(1,2-dioxo-2-(phenylamino)ethyl)methylamino]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-[(1,2-dioxo-2-(methylamino)ethyl)methylamino]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.