Facile one-pot,three-component synthesis of novel bis(heterocycles) incorporating thieno[2,3-b]thiophenes via Michael addition reaction

A synthesis of novel series of bis(2-amino-3-cyano-4H-chromene), bis(2-amino-3-cyanopyrano3,2-c]chromene), bis(6-amino-5-cyano-1,4-dihydropyrano2,3-c]pyrazole), and bis(2,7-diamino-3,4,6-tricyanopyrazolo1,5-a]pyridine) derivatives linked to thieno2,3-b]thiophene core via ether or ester linkages was reported. The formation of the target compounds presumably proceeds through a three component reaction of the appropriate bis(aldehyde) with 2 M of each of malononitrile and the corresponding active methylene compounds namely; dimedone, 4-hydroxycoumarine, 5-methyl-2,4-dihydro-3H-pyrazol-3-one, or cyanomethylpyrazole in dioxane at reflux in the presence of piperdine as a basic catalyst. The chemical structures of the new compounds were elucidated by several spectral tools.