Cycloaddition of benzoheteroazepineⅢ reaction of 2,3-dihydro-1 H-1,5-benzodiazepines with dichlorocarbene and stereo-structures of products

摘要

Reaction of 2,3-dihydro-1 H-1, 5-benzodiazepines with dichlorocarbene generated in situ using benzyltriethylammonium chloride(TEBA)as a phase transfer catalyst in chloroform-aqueous sodium hydroxide mixture gave mainly 1,2-cycloadducts, cis and trans-1a, 3-disubstituted-1,1-dichloro-1a, 2,3,4-tetrahydro-1 H- azirono[1,2-a][1,5]benzodiazepines(2,3), and formylated 1,2-cycloadducts, trans-1a, 3-disubstituted-1, 1- dichloro-4-formyl-1a, 2,3,4-tetrahydro-1 H-azirino[1,2-a][1,5]benzodiazepines(4). The stereo-structures of cyloadducts and the mechanism are also discussed..