Synthesis of 6,12-Epiminodibenzo[b,f][1,5]diazocines via an Ytterbium Triflate-Catalyzed, AB Three-Component Reaction.
, Karuppasamy M
, Nagarajan S
, Maheswari CU
, Pace V
, Menéndez JC
, Sridharan V
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An efficient and selective procedure for the synthesis of epiminodibenzo[b,f][1,5]diazocines involving a AB three-component reaction is developed. Two equivalents of suitably substituted 2-aminoarylaldehydes reacted with arylamines in the presence of Yb(OTf) to 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.
PMID: 27682636 [PubMed]
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