280113-69-1Relevant articles and documents
Synthesis of 6,12-Epiminodibenzo[b,f][1,5]diazocines via an Ytterbium Triflate-Catalyzed, AB2 Three-Component Reaction
Muthukrishnan, Isravel,Karuppasamy, Muthu,Nagarajan, Subbiah,Maheswari, C. Uma,Pace, Vittorio,Menéndez, J. Carlos,Sridharan, Vellaisamy
, p. 9687 - 9694 (2016)
An efficient and selective procedure for the synthesis of epiminodibenzo[b,f][1,5]diazocines involving a AB2 three-component reaction is developed. Two equivalents of suitably substituted 2-aminoarylaldehydes reacted with arylamines in the presence of Yb(OTf)3 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.
Synthesis of tricyclic aromatic compounds by the intramolecular Pauson-Khand reaction promoted by molecular sieves
Perez-Serrano, Leticia,Blanco-Urgoiti, Jaime,Casarrubios, Luis,Dominguez, Gema,Perez-Castells, Javier
, p. 3513 - 3519 (2007/10/03)
Pauson-Khand reactions are carried out with different substituted aromatic enynes, yielding tricyclic cyclopentenones related to natural products such as chromenes. Enynes are easily obtained in a two-step approximation from the corresponding salicylaldehydes. The reaction is promoted by dissolved TMANO (trimethylamine N-oxide) and/or 4 A molecular sieves. This new way of induction for the Pauson-Khand reaction increases yields remarkably, allowing the reaction of some substituted alkenes which fail to react in the absence of the zeolite. Isomerization of the double bond of the cyclopentenone ring is observed except when nonterminal triple bonds are used. For trisubstituted alkenes, an interrupted Pauson-Khand process is observed with moderate yields.