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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

Ch Gurumurthy, Narjis Fatima, G Narender Reddy, C Ganesh Kumar, Gowravaram Sabitha, K V S Ramakrishna

Bioorg Med Chem Lett. 2016 Oct 15;26(20):5119-5125.

PMID: 27624077

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP7787602 Bismuth(III) chloride Bismuth(III) chloride 7787-60-2 Price
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