Tetrahedron

The preparation of aromatic amidino esters and their reaction with primary amines

JT Gupton, JF Miller, RD Bryant, PR Maloney…

Index: Gupton, John T.; Miller, John F.; Bryant, Robert D.; Maloney, Patrick R.; Foster, Bruce S. Tetrahedron, 1987 , vol. 43, # 8 p. 1747 - 1752

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Citation Number: 12

Abstract

A series of aromatic amidino esters were prepared from the respective anthranilic acids by reaction with DMF acetal. These amidino esters were then condensed with a variety of primary amines to give the corresponding 3-substituted quinazolin-4-ones. Based on substituent effects, and the application of acid catalysis, a unifying mechanism is proposed.