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Neue 1,5‐benzodiazepinderivate
Author(s) -
Capuano Lilly,
Gärtner Klaus
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180713
Subject(s) - chemistry , diazo , methylene , isocyanate , phenyl isocyanate , medicinal chemistry , nitrogen , group (periodic table) , azo coupling , stereochemistry , organic chemistry , polymer chemistry , polyurethane
The 1,5‐benzodiazepines 1,6 add benzoylphenylketene ( 3 ) across the azomethine bond to produce the 1,3‐oxazino[3,2‐ a ]‐1,5‐benzodiazepines 4,5,7. In 6a azo coupling occurs at the exocyclic methyl group leading to the formation of 10 , while diazo group transfer takes place at the cyclic methylene group to afford 11. The latter compounds react with 3 without loss of the diazo nitrogen, yielding the diazo‐oxazinobenzodiazepine 12 ; whereas, by interaction with phenyl isocyanate, the pyrazolo[4,3‐ b ]‐1,5‐benzodiazepine 14 is formed.
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