Molecular diversity of three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones

Abstract

The three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 2-arylidene-1,3-indanediones showed very interesting molecular diversity. The three-component reaction in refluxing acetonitrile afforded functionalized spiro[furan-2,1′-indene] derivatives. On the other hand, the three-component reaction in refluxing ethanol gave functionalized cyclopenta[b]naphthalene derivatives. In addition, the similar three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5-arylidene-N,N′-dimethylbarbituric acids resulted in functionalized diazaspiro[4.5]deca-1,3-diene-1,2-dicarboxylates in satisfactory yields. A plausible reaction mechanism including in situ of Huisgen's 1,4-dipole, and sequential annulation reaction was proposed to explain the formation of the different polycyclic compounds.