Substituted pyridinium-3-sulfonamidates and pyrido[3,4-b]indoles from 2-aryl-3,5-dimethyl-1,1-dioxo-1,2-thiazine-6-carbaldehydes and amines [German]

摘要

Due to their masked 1,5-dicarbonyle structure, 1,2-thiazine-6-carbaldehydes (1) undergo a ring transformation with aliphatic amines and diamines to give substituted pyridinium-3-sulfonamidates 2-6 and bis-(pyridinium-3-sulfonamidates) 7-9, respectively. With bioactive beta-substituted ethylamines, pyridinium derivatives 12-20 with potential biological activity were obtained. Under acidic conditions, the thiazine-6-carbaldehydes 1a-d react with tryptamine to give substituted 9H-tetrahydropyrido[3,4-b]indoles 22a-d (Harman type alcaloids). 22a was dehydrogenated to the corresponding pyrido-indole 23a by palladium coal. [References: 10]