Synthesis of substituted 1, 2-dihydroisoquinolines via Ni(ii) and Cu(i)/Ag(i) catalyzed double nucleophilic addition of arylamines to ortho-alkynyl donor–acceptor cyclopropanes (o-ADACs). Issue 27 (22nd June 2021)

• Record Type: Journal Article
• Authors: Unnava, Ramanjaneyulu; Chahal, Kapil; Reddy, Kallu Rajender
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 27(2021)
• Page Start: 6025
• Page End: 6029
• Publication Date: 2021-06-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob00760b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Synthesis of substituted 1, 2-dihydroisoquinolines via double nucleophilic addition of primary arylamines to ortho -alkynyl donor–acceptor cyclopropanes ( o -ADACs) in the presence of a catalytic Ni(ii ) and Cu(i )/Ag(i ) system has been developed. Abstract : A concise approach for the synthesis of substituted 1, 2-dihydroisoquinolines via double nucleophilic addition of primary arylamines to ortho -alkynyl donor–acceptor cyclopropanes ( o -ADACs) in the presence of a catalytic Ni(ClO4 )2 ·6H2 O and CuI/AgOTf system has been developed. Further applying this protocol, some of the derived malonates were converted into the corresponding monoesters under Krapcho decarboxylation reaction conditions. Thereafter, these esters were transformed into the respective acids and alcohols. In addition, multifunctionalized 4-(2, 2, 2-trifluoroacetyl) 1, 2-dihydroisoquinolines were also obtained with excess TFAA.