Tetrahedron

Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs

S Papot, C Bachmann, D Combaud, JP Gesson

Index: Papot, Sebastien; Bachmann, Christian; Combaud, Damien; Gesson, Jean-Pierre Tetrahedron, 1999 , vol. 55, # 15 p. 4699 - 4708

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Citation Number: 6

Abstract

Unsubstituted N-arylcarbamate of title compound does not cyclize to the corresponding cyclic urea, with ROH liberation, under mild conditions (40° C). Substitution of the benzylic position by two methyl groups promotes slow cyclisation while N-methylation of the N-aryl carbamate has a more important effect. Relative cyclisation rates are in agreement with barrier heights obtained from ab initio calculations. The calculations also suggest that the ...