Premium
Arene imine derivatives of chrysene and of benzo[ g ]chrysene: 1a,11c‐dihydrochryseno[5,6‐ b ]azirine and 1a,13c‐dihydrobenzo[11,12]chryseno[5,6‐ b ]azirine
Author(s) -
AbuShqara Elias,
Elg'Amal Shafea,
Blum Jochanan
Publication year - 1990
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.5570270631
Subject(s) - chemistry , azirine , chrysene , medicinal chemistry , nitroso , organic chemistry , ring (chemistry) , pyrene
The syntheses of the K‐iraines (which are also benzo‐bay‐region derivatives) of chrysene ( 1 ) and benzo[ g ]‐chrysene ( 2 ) are described. The preparation of 1a,11c‐dihydrochryseno[5,6‐ b ]azirine ( 5 ) was accomplished by treatment of 1a,11c‐dihydrochryseno[5,6‐ b ]oxirene ( 4 ) with sodium azide, and the mixture of trans ‐azido‐alcohols 6 and 7 , so formed, was either cyclized with triethyl phosphite, or converted into E ‐6‐azido‐5‐chloro‐5,6‐dihydrochrysene ( 8 ) followed by lithium aluminium hydride reduction. The synthesis of 1a,13c‐dihydrobenzo‐[11,12]chryseno[5,6‐ b ]azirine ( 12 ) included the transformation of the corresponding oxide 11 into a mixture of E ‐9‐azido‐9,10‐dihydrobenzo[ g ]chrysen‐10‐ol ( 13 ) and E ‐10‐azido‐9,10‐dihydrobenzo[ g ]chrysen‐9‐ol ( 14 ), and reaction with tri‐ n ‐butylphosphine to give a mixture of Staudinger adducts 15 and 16 that underwent thermal decomposition into 12 upon heating in boiling dichloromethane.