REACTIONS OF 2-(LITHIOMETHYL)PHENYL ISOCYANIDES WITH METHYL 1-METHYLINDOLE-3-CARBOXYLATE: ELABORATIONS OF THE ADDUCTS TO 5H-BENZ[2,3]AZEPINO[5,6-c]INDOL-12-ONE AND 2,3'-BIINDOLYL DERIVATIVES

摘要

It has been found that when 2-(lithiomethyl)phenyl isocyanides were allowed to react with methyl 1-methylindole-3-carboxylate, the corresponding 1,4-and/or 1,2-adducts were obtained. The 1,4-adducts could be transformed into 6,11-dihydro-5H-benz[2,3]azepino[5,6-b]indol-12-ones derivatives by acid hydrolysis, followed by lactamization and subsequent dehydrogenation. The transformation of the 1,2-adducts into 2,3'-biindolyls was accomplished by a sequential treatment with hydrochloric acid and aqueous sodium hydroxide.