Lewis acid promoted dual bond formation: facile synthesis of dihydrocoumarins and spiro-tetracyclic dihydrocoumarins.
Lewis acid (FeCl3) mediated dual bond (C-C and C-O) formation for synthesis of 3,4-dihydrocoumarins is presented. This method has successfully delivered a number of dihydrocoumarins containing dense functionalities on the aromatic ring. Significantly, the present method enabled achieving dihydrocoumarins with tertiary as well as quaternary carbon atoms at the benzylic position. Gratifyingly, the novel spiro-tetracyclic lactones have also been dextrously prepared using this process.
Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Ordnance Factory Estate Campus, Yeddumailaram - 502 205, Medak District, Andhra Pradesh, India. gvsatya@iith.ac.in.
Pedireddi
P
Niharika
Bokka Venkat
BV
Ramulu
Gedu
G
Satyanarayana
D002625:Chemistry, Organic / Q000379:methods*; D002934:Cinnamates / Q000737:chemistry; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D058116:Lewis Acids / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002934:Cinnamates; D003374:Coumarins; D058116:Lewis Acids; D011083:Polycyclic Compounds; C029010:cinnamic acid