6 research outputs found
One-Pot Synthesis of 2-(Aryl/Alkyl)amino-3-cyanobenzobthiophenes and Their Hetero-Fused Analogues by Pd-Catalyzed Intramolecular Oxidative C�H Functionalization/Arylthiolation
We have developed a high-yielding synthesis for substituted 2-(aryl/alkyl)amino-3-cyanobenzobthiophenes and their hetero-fused analogues by using a palladium-catalyzed intramolecular oxidative C�H functionalization/arylthiolation reaction of in situ generated N-(alkyl/aryl)thioamides, prepared from readily available (hetero)arylacetonitriles and alkyl/aryl isothiocyanates. This protocol was then extended to the synthesis of amino-substituted benzothieno2,3-bquinolines by employing a triflic acid mediated intramolecular cyclocondensation of the prepared 2-arylamino-3-cyanobenzobthiophenes. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinhei
A metal-free, one-pot route to substituted benzobthiophenes and their hetero-fused analogs via iodine mediated intramolecular arylthiolation of in situ generated β-(het)aryl-β-cyanoenethiolates
A metal-free one-pot route to substituted 3-cyanobenzo. bthiophenes has been developed via iodine mediated intramolecular arylthiolation of 2-(het)aryl-2-cyanoenethiolates generated in situ by base mediated condensation of arylacetonitriles and (het)aryl dithioesters. The methodology has been further extended to the synthesis of 2-aminobenzo. bthiophenes as well as hetero-fused thiophenes such as thieno2,3-bthiophenes, thieno2,3-bindoles and thieno3,2-cpyrazoles. An electrophilic cyclization mechanism has been proposed based on experimental observations. © 2017 Elsevier Ltd