Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C-N bond-forming reaction

Abstract

The coupling of bromothiophenes with terminal alkynes using triethylamine or diisopropyl amine under Sonogashira conditions (PdCl2(PPh 3)2, CuI) followed by subsequent addition of amines or ammonium to the intermediate thienyl acetylenes represents a novel access to a wide range of thieno[3,2-b]-, [2,3-c]-, and [3,2-c]pyridones under basic conditions and in excellent yields. © 2013 Elsevier Ltd. All rights reserved.