Deamination of naphthalen-1,4-imines and anthracen-9,10-imines by reaction with benzyne or dimethyl acetylenedicarboxylate

Abstract

Bridging N-methyl or N ethyl groups are lost from 1,4,5,8-tetrasubstituted 1,4-dihydro-1,4-epiminonaphthalene-2,3-dicarboxylates by reaction with dimethyl acetylenedicarboxylate to give the corresponding naphthalene compounds. Some 9,10-dihydro-9,10-epiminoanthracene derivatives react similarly with benzyne or with the acetylenic ester to give the corresponding anthracene and/or its Diels–Alder adduct with the same dienophile.