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The syntheses of 4b,5a‐dihydro‐5 H ‐benzo[3,4]‐phenanthro[1,2‐ b ]azirine and 1a,11b‐dihydro‐6,11‐dimethyl‐1 H ‐benz[3,4]anthra[1,2‐ b ]azirine
Author(s) -
AbuShqara Elias,
Blum Jochanan
Publication year - 1989
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.5570260220
Subject(s) - chemistry , azirine , thionyl chloride , medicinal chemistry , lithium aluminium hydride , aluminium chloride , lithium (medication) , imine , stereochemistry , chloride , organic chemistry , aluminium , ring (chemistry) , catalysis , medicine , endocrinology
The syntheses of the K‐imine derivatives of carcinogenic benzo[ c ]phenanthrene and 7,12‐dimethylbenz‐[ a ]anthracene are described. Treatment of trans ‐5‐azido‐5,6‐dihydrobenzo[ c ]phenanthren‐6‐ol ( 3 ) and trans ‐6‐azido‐5,6‐dihydrobenzo[ c ]phenanthren‐5‐ol ( 5 ) with thionyl chloride yielded the corresponding β‐chloro azides, which in turn, were reacted with lithium aluminium hydride to give 4b,5a‐dihydro‐5 H ‐benzo[3,4]‐phenanthro[1,2‐ b ]azirine ( 2 ). In a similar manner trans ‐5‐azido‐5,6‐dihydro‐7,12‐dimethylbenz[ a ]anthracen‐6‐ol ( 11 ) and trans ‐6‐azido‐5,6‐dihydro‐7,12‐dimethylbenz[ a ]anthracen‐5‐ol ( 13 ) were transformed to the respective chloro azides and, converted into 1a,11b‐dihydro‐6,11‐dimethyl‐1 H ‐benz[3,4]anthra[1,2‐ b ]azirine ( 10 ).