Unprecedented bridged annulation approach to the construction of 5,6-dihydro-4H-benzo[kl]acridines.
A general and novel "bridged annulation" methodology for the synthesis of 5,6-dihydro-4H-benzo[kl]acridines has been developed via Michael addition of a conjugate base of 9-methyl-3,4-dihydroacridin-1(2H)-one to various cyclic or acyclic alpha,beta-unsaturated carbonyl/nitrile compounds under mild conditions at room temperature in a short time. To the best of our knowledge, such a general bridged annulation for the synthesis of fused N-heterocycles has not been reported in the literature.
Goel
Atul
A
Division of Medicinal and Process Chemistry, Central Drug Research Institute, CSIR, Lucknow 226001, India. atul_goel@cdri.res.in
Singh
Salil Pratap
SP
Kumar
Amit
A
Kant
Ruchir
R
Maulik
Prakas R
PR
D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
C546263:5,6-dihydro-4H-benzo(kl)acridine; D000166:Acridines; D000447:Aldehydes; D009570:Nitriles