Synthesis of the Non-K-Region Dihydrodiols of 7-Methylbenzacridine

Article abstract of DOI:10.1021/jo00197a022

The synthesis of the four non-K-region trans-dihydrodiols of 7-methylbenzacridine (2) are described.The trans-8,9- and -10,11-dihydrodiols 13 and 16 were prepared from 7-methyl-8,9,10,11-tetrahydrobenzacridine (3) via the trans-8,9-diacetoxy-7-methyl-8,9,10,11-tetrahydrobenzacridine (10) and its 10,11-isomer (14) by selective benzylic bromination followed by dehydrobromination.The trans-tetrahydro diacetates were obtained through the alkenes 6 and 7 and their epoxide derivatives. trans-1,2- and -3,4-dihydrodiols 22 and 24 were similarly prepared from the trans-1,2- and -3,4-diacetates of 7-methyl-1,2,3,4-tetrahydrobenzacridine (19 and 20).The latter were products of the Prevost reaction on mixed 3,4- and 1,2-dihydro-7-methylbenzacridines (17 and 18).