An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

Abstract

A series of novel bis (thieno[2,3-b]pyridines) based arenes or heteroarenes have been synthesized from the appropriate bisbromoacetyl derivatives upon treatment with the corresponding 2-mercaptonicotinonitrile derivatives in ethanolic sodium ethoxide at reflux. Attempts to synthesize these compounds via bis-alkylation of the appropriate phenol derivative with the corresponding dibromo compounds using a mild base were unsuccessful.

Utility of 2-Chloro-N-arylacetamide and 1,1′-(Piperazine-1,4-diyl)bis(2-chloroethanone) as Versatile Precursors for Novel Mono- and Bis[thienopyridines]

“…It is suggested that compound 17 was formed initially and then intramolecular cyclocondensation of the methylene group with the ketonic groups at the 2-position of thienopyridine leading to the formation of the corresponding 2-bezofuranyl derivative 18 followed by hydrolysis and subsequent decarboxylation under the reaction conditions to give 19 . Similar behavior of some related systems has been previously reported …”

“…Similar behavior of some related systems has been previously reported. 82 It is worth mentioning that treatment of 15a under similar conditions gave a mixture of nonisolable products.…”