A diastereoselective synthesis of tetrahydro- and dihydro-pyrido[2,3-c]coumarin derivatives via a one-pot three-component Povarov reaction catalyzed by bismuth(III) chloride.
A diastereoselective synthesis of tetrahydro- and dihydro-pyrido[2,3-c]coumarin derivatives has been achieved via a one-pot three-component aza-Diels-Alder reaction of aromatic aldehydes, 3-aminocoumarin and dienophiles catalyzed by BiCl3. NOE studies proved that exo-isomers were obtained in all cases with high selectivity. The reaction proceeded at room temperature providing good yields of products as well as applicability on a wide range of substrates. Among all the synthesized derivatives, compounds 4i and 4k showed promising DPPH radical scavenging activity as compared to other tested derivatives.
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), New Delhi, India.
Ch
C
Gurumurthy
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Narjis
N
Fatima
Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
G Narender
GN
Reddy
Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
C Ganesh
CG
Kumar
Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India. Electronic address: gowravaramsr@yahoo.com.
Gowravaram
G
Sabitha
NMR Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
K V S
KVS
Ramakrishna
D001729:Bismuth / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000494:pharmacology*; D013237:Stereoisomerism
D003374:Coumarins; D016166:Free Radical Scavengers; D001729:Bismuth
Aza-Diels–Alder; Bismuth(III) chloride; DPPH radical scavenging; Diastereoselective; Pyrido[2,3-c]coumarins