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.
Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.
p. 1513 - 1518
(2007/10/02)
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