Synthesis of functionalized coumarins and quinolinones by NHC-catalyzed annulation of modified enals with heterocyclic C-H acids.
N-Heterocyclic carbene (NHC) catalyzed lactonization and lactamization of 2-bromoenals with heterocyclic C-H acids proceeding via the α,β-unsaturated acyl azolium intermediates is reported. The reaction furnished coumarin- or quinolinone-fused lactone/lactam derivatives. In addition, results of the enantioselective version of this reaction using chiral NHC are presented.
Organic Chemistry Division, C SIR-National Chemical Laboratory (CSIR-NCL) , Dr. Homi Bhabha Road, Pune 411008, India.
Santhivardhana Reddy
SR
Yetra
Tony
T
Roy
Anup
A
Bhunia
Digvijay
D
Porwal
Akkattu T
AT
Biju
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry
D000143:Acids; D003374:Coumarins; D006571:Heterocyclic Compounds; D015363:Quinolones; C030011:carbene; D008697:Methane