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Cycloaddition of benzoheteroazepine II Reactions and conformations of cycloadducts on 1, 5‐benzothiazepines and 1,5‐benzodiazepines with nitrile imine and nitrile oxides
Author(s) -
Xu JiaXi,
Wu HaiTao,
Jin 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.19990170112
Subject(s) - chemistry , benzonitrile , nitrile , cycloaddition , imine , benzodiazepine , medicinal chemistry , 1,3 dipolar cycloaddition , benzazepines , tricyclic , stereochemistry , organic chemistry , catalysis , biochemistry , receptor
Benzodiazepine and benzothiazepine derivatives have been well known as therapeutically important compounds. Four new tricyclic heterocyclic compounds, 3a, 4, 5, 11‐tetrahydro‐3 H ‐l,2, 4‐triazalo [4, 3‐ d ] [1, 5] benzothiazepines (3), 3a, 4, 5, 11‐tetrahydro‐3 H ,6 H ‐1, 2, 4‐triazolo[4, 3‐ d ] [1, 5]benzodiazepine (4), 3a, 4, 5, 11‐tetrahydro‐1, 2, 4‐oxadiazolo [4, 5‐ d ] [1, 5]benzothiazepines (5, 6) and 3a,4, 5, 11‐tetrahydro‐6 H ‐1, 2, 4‐oxadiazolo[4, 5 ‐d ] [1, 5] benzodiazepines (7, 8), have been synthesized by 1, 3‐dipolar cycloaddition reactions of 2, 3‐dihydro‐1, 5‐benzothiazepines and 2, 3‐dihydro‐1 H ‐1, 5‐benzodiazepine with benzonitrile N‐ phenylimine and benzonitrile oxides, receptively. The conformations of some cycloadducts and cycloaddition mechanism are described.