A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction.
An efficient method towards the synthesis of quinoline fused tricyclic compounds involving an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction utilizing Baylis-Hillman derivatives in good yields has been described for the first time. A highly functionalized tricyclic framework was created by forming two rings and two adjacent stereocentres through the formation of two N-C bonds, one C-C bond and one O-C bond in a highly regio and diastereoselective manner.
Department of Chemistry, Pondicherry University, Pondicherry-605 014, India. bhakthadoss@yahoo.com.
Manickam
M
Bakthadoss
Varathan
V
Vinayagam
D061565:Cycloaddition Reaction; D008958:Models, Molecular; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009570:Nitriles; D010087:Oxides; D011804:Quinolines; C542964:1,2,3,4-tetrahydroquinoline