Synthesis of 6,12-Epiminodibenzo[b,f][1,5]diazocines via an Ytterbium Triflate-Catalyzed, AB2Three-Component Reaction.
An efficient and selective procedure for the synthesis of epiminodibenzo[b,f][1,5]diazocines involving a AB2three-component reaction is developed. Two equivalents of suitably substituted 2-aminoarylaldehydes reacted with arylamines in the presence of Yb(OTf)3to afford the desired products in high yields. The reaction is highly atom-economic and waste-free, in addition to allowing the generation of two heterocyclic rings and four C-N bonds in a single operation. Significantly, this approach is complementary to the existing literature procedures, affording arylamine-derived products that could not be accessed previously. A plausible mechanism is proposed involving an imine formation-intermolecular annulation-intramolecular iminium ion cyclization sequence.
Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur, Tamil Nadu 613401, India.
Isravel
I
Muthukrishnan
Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur, Tamil Nadu 613401, India.
Muthu
M
Karuppasamy
Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur, Tamil Nadu 613401, India.
Subbiah
S
Nagarajan
Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur, Tamil Nadu 613401, India.
C Uma
CU
Maheswari
Department of Pharmaceutical Chemistry, University of Vienna , Althanstrasse 14, A-1090 Vienna, Austria.
Vittorio
V
Pace
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense , 28040 Madrid, Spain.
J Carlos
JC
Menéndez
Organic Synthesis Group, Department of Chemistry, School of Chemical and Biotechnology, SASTRA University , Thanjavur, Tamil Nadu 613401, India.
Vellaisamy
V
Sridharan