Synthesis of 3-Amino-4-(3H)-quinazolinones from N-(2-Carbomethoxyphenyl) Imidate Esters

Article abstract of DOI:10.1021/jo00216a023

Novel difunctional aromatic synthons consisting of N-(2-carbomethoxyphenyl) imidate esters were synthesized by treatment of methyl anthranilate esters with aliphatic ortho esters.Treatment of the imidates with hydrazine, methylhydrazine, and phenylhydrazine yielded only quinazolinones and not isomeric 1,3,4-benzotriazepin-5-ones.The type of products obtained gave information relevant to elucidation of the mechanism of cyclization and the relative reactivities of the ester and imidate groups.