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).

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)2·6H2O 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.