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The reaction of 1‐azirines with 2‐pyridyl isothiocyanate: Possible approaches to benzodiazepine and benzodiazepine derivatives
Author(s) -
Nair V.,
Kim K. H.
Publication year - 1976
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.5570130434
Subject(s) - chemistry , isothiocyanate , pyridazine , azide , cycloaddition , azirine , pyrrole , thermal decomposition , pyrazine , dimer , phenyl isothiocyanate , medicinal chemistry , benzodiazepine , ring (chemistry) , stereochemistry , organic chemistry , catalysis , biochemistry , receptor
The structure of the dimer ( 5 ) from 2‐pyridyl isothiocyanate ( 1 ) has been confirmed by 13 C nmr spectral studies. The cycloaddition of 2‐pyridyl isothiocyanate with 1‐azirines results in the formation of thiazoles ( 10 ). Thermal decomposition of the vinyl azide ( 14 ) gives the pyrrole ( 15 ) and the pyridazine ( 16 ) instead of 2‐(2‐pyridyl)‐1‐azirine ( 12 ).