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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