title: Sequential coupling/desilylation-coupling/cyclization in a single pot under Pd/C-Cu catalysis: synthesis of 2-(hetero)aryl indoles.
abstract: A new one-pot synthesis of 2-(hetero)aryl indoles via sequential C-C coupling followed by C-Si bond cleavage and a subsequent tandem C-C/C-N bond forming reaction is described. A variety of functionalized indole derivatives were prepared by conducting this four step reaction under Pd/C-Cu catalysis. The methodology involved coupling of (trimethylsilyl)acetylene with iodoarenes in the presence of 10% Pd/C-CuI-PPh(3) and triethylamine in MeOH, followed by treating the reaction mixture with K(2)CO(3) in aqueous MeOH, and finally coupling with o-iodoanilides. The single crystal X-ray data of a synthesized indole derivative is presented. Application of the methodology, in vitro pharmacological properties of the synthesized compound, along with a docking study is described.
authors: Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad, Andhra Pradesh, India.
authors: R Mohan
authors: RM
authors: Rao
authors: Upendar C H
authors: UC
authors: Reddy
authors: Alinakhi
authors: Naveen
authors: N
authors: Mulakayala
authors: Mallika
authors: M
authors: Alvala
authors: M K
authors: MK
authors: Arunasree
authors: Rajamohan R
authors: RR
authors: Poondra
authors: Javed
authors: J
authors: Iqbal
authors: Manojit
authors: M
authors: Pal
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D004789:Enzyme Activation / Q000187:drug effects; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D056564:Sirtuin 1 / Q000378:metabolism
chemical_list: D007211:Indoles; D010165:Palladium; D002244:Carbon; D003300:Copper; C447939:SIRT1 protein, human; D056564:Sirtuin 1; D012825:Silicon