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

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• 作者：Ch. Gurumurthy^a ; ^d ; Narjis Fatima^a ; G. Narender Reddy^b ; C. Ganesh Kumar^b ; Gowravaram Sabitha^a ; ^{gowravaramsr@yahoo.com" class="auth_mail" title="E-mail the corresponding author} ; ^{sabitha@iict.res.in" class="auth_mail" title="E-mail the corresponding author} ; K.V.S. Ramakrishna^c
• 关键词：Diastereoselective ; Bismuth(III) chloride ; Pyrido[2 ; 3-c]coumarins ; DPPH radical scavenging ; Aza-Diels&ndash ; Alder
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 October 2016
• 年：2016
• 卷：26
• 期：20
• 页码：5119-5125
• 全文大小：3788 K

文摘

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.