A rapid and simple diversity-oriented synthesis of novel 3-amino-2 '-oxospiro [benzo[c]pyrano[3,2-a]phenazine-1,3 '-indoline]-2-carbonitrile/carboxylate derivatives via a one-pot, four-component domino reaction

作者：Mahdavinia Gholam Hossein^*; Mirzazadeh Maryam; Notash Behrouz

来源：Tetrahedron Letters, 2013, 54(27): 3487-3492.

DOI：10.1016/j.tetlet.2013.04.082

• One-pot
• Four-component
• DABCO
• Regioselective
• Domino reaction
• Diversity-oriented synthesis

An efficient regio- and chemoselective method for the synthesis of novel 3-amino-2'-oxospiro[benzo[c]pyrano[3,2-a]phenazine-1,3'-indoline]-2-carbonitrile/carboxylate derivatives has been developed via the one-pot, four-component domino coupling of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, isatins, and malononitrile/cyanoacetic ester in the presence of DABCO under reflux conditions in excellent yields. The merit of this cascade formation of two C=N bonds/Knoevenagel condensation/Michael addition/cyclization sequence is highlighted by its high atom-economy, excellent yields, efficiency of producing five new bonds (two C-N, two C-C, and one C-O), and one stereocenter in a single operation.

• 出版日期2013-7-3