Cascade process for direct synthesis of indeno[1,2-b]furans and indeno[1,2-b]pyrroles from diketene and ninhydrin

• DOI: 10.1007/s11030-019-09996-7
• Publication Date: 2019-10-01T20:04:15Z
• Authors: Atieh Rezvanian; Fatemeh Moradi; Vahideh Zadsirjan; Masoumeh Mohammad...; Majid M. Heravi
• Keywords: Ninhydrin; Diketene; Furan; Indane; Cascade reaction

Novel and efficient multicomponent reactions (MCRs) involving diketene, ninhydrin (indane-1,2,3-trione) and one primary amine (3CR) or two different primary amines (4CR) were achieved for the successful synthesis of dihydro-4H-indeno[1,2-b]furan-3-carboxamides or tetrahydroindeno[1,2-b]pyrrole-3-carboxamides, respectively. The merits of this method are highlighted by using either commercially available or easily accessible starting materials, operational simplicity, facile workup procedure, efficient usage of all the reactants, tolerance of a variety of functional groups and ability to conduct under un-catalyzed reaction condition. The products were also isolated by just decantation of the solvent, and for the purification column chromatography was non-required.