1137270-41-7Relevant academic research and scientific papers
Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1-a]-Isoquinolines via Rh(III)-Catalyzed C?H Functionalizations of 2-Arylindoles with Sulfoxonium Ylides
Chen, Guang,Zhang, Xinying,Jia, Ruixue,Li, Bin,Fan, Xuesen
, p. 3781 - 3787 (2018)
A highly chem- and regioselective synthesis of diversely substituted benzo[a]carbazoles and indolo[2,1-a]-isoquinolines through Rh(III)-catalyzed cascade reactions of 2-arylindoles with sulfoxonium ylides is presented. To be specific, treatment of 2-arylindoles, 2-arylindole-3-carbaldehydes, 2-arylindole-3-carbonitriles or 2-aryl-3-methylindoles with sulfoxonium ylides under the catalysis of Rh(III) led to the selective formation of 6-aryl/alkyl benzo[a]carbazoles, 5-acylbenzo[a]carbazoles, 6-amino-5-acylbenzo[a]carbazoles or 12-methylindolo[2,1-a]isoquinolines, respectively. Mechanistically, the formation of the title compounds involves a cascade process including metalation of the inert C(sp2)?H bond, migratory insertion of ylide into the carbon-metal bond via an in situ carbenoid formation, protodemetalation, and condensation. To our knowledge, this is the first example in which β-carbonyl sulfoxonium ylides were used as stable carbene precursors and bifunctional C2 synthons to afford benzo[a]carbazoles and indolo[2,1-a]isoquinolines. (Figure presented.).
Base-mediated regio- and stereoselective intermolecular addition of alkynes to N-heterocycles
Verma, Akhilesh Kumar,Joshi, Megha,Singh, Ved Prakash
scheme or table, p. 1630 - 1633 (2011/05/03)
The regio- and stereoselective addition of N-heterocycles to alkynes using KOH is reported. Formation of (Z)-isomers and their conversion to (E)-products were found to be dependent upon time as well as the choice of base. Selective attack of N-heterocycles on a more electrophilic alkynyl carbon was supported by DFT calculations, and the stereochemistry of the products was established by X-ray crystallographic studies and intramolecular cyclization of ortho-haloalkynes in indolo-[2,1-a]isoquinolines.
A copper-catalyzed tandem synthesis of indolo- and pyrrolo[2,1-a] isoquinolines
Verma, Akhilesh Kumar,Kesharwani, Tanay,Singh, Jaspal,Tandon, Vibha,Larock, Richard C.
supporting information; experimental part, p. 1138 - 1143 (2009/06/20)
(Chemical Equation Presented) Isoquinoline ring the changes: A novel strategy for the title reaction involves ortho-haloarylalkynes which undergo sequential intermolecular addition of N heterocycles onto alkynes and subsequent intramolecular ring closure by arylation. The process involves the use of hydroxymethyl benzotriazole as an efficient and inexpensive ligand for the C - N and C - C coupling reactions.
