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Syntheses of benzo[b]‐ and benzo[j]phenanthridines

 

作者: L. H. Klemm,   Annekäte Weisert,  

 

期刊: Journal of Heterocyclic Chemistry  (WILEY Available online 1965)
卷期: Volume 2, issue 1  

页码: 15-20

 

ISSN:0022-152X

 

年代: 1965

 

DOI:10.1002/jhet.5570020104

 

出版商: Wiley‐Blackwell

 

数据来源: WILEY

 

摘要:

AbstractThe isomeric lactams benzo[b]phenanthridine‐5(6H)‐one and benzo[j]phenanthridine‐6(5H)‐one were obtained in equal yields by Schmidt reaction on 11H‐benzo[b]fluoren‐11‐one (44% total) or by Beckmann reaction on 11H‐benzo[b]fluoren‐11‐one oxime (22% total). Reduction of the lactams with lithium aluminum hydride gave the 5, 6‐dihydro‐benzo[b]‐ and ‐[j]phenanthridines. Dehydrogenation of these dihydro derivatives produced the parent aromatic heterocycles benzo[b]‐ and benzo[j]phenanthridine in best overall yields of 20% and 12%, respectively. A few substituted benzophenanthridines were also prepared. Assignment of structures was based on ultraviolet, infrared, and n.m.r. spectra of the dihydro derivatives as well as on separate unequivocal synthesis of the

 

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