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Cycloaddition of benzoheteroazepine III Reaction of 2,3‐dihydro‐1 H ‐15benzodiazepines with dichlorocarbene and stereo‐structures of products
Author(s) -
Zhang XinYu,
Xu JiaXi,
Jem Sheng
Publication year - 1999
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19990170414
Subject(s) - dichlorocarbene , chemistry , cycloaddition , medicinal chemistry , stereochemistry , organic chemistry , catalysis
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 ‐azirino[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, 4–1 H ‐azirino[1, 2‐ a ][1, 5]benzodiacepines (4). The stereo‐structures of cycloadducts and the mechanism are also discussed.