Helvetica Chimica Acta, ( ISI ), Volume (95), Year (2012-4) , Pages (52-60)

Title : ( Synthesis of 1H,7H,12bH-Pyrano[3’,4’: 5,6]pyrano[3,4-c][1]benzopyran-1- one via Domino Knoevenagel/Hetero-DielsAlder Reaction with Theoretical Investigations )

Authors: Malihe Javan Khoshkholgh , Mohammad Reza Housaindokht , Saeed Balalaie , Mohammad Reza Bozorgmehr , Hamid Reza Bijanzadeh ,
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Abstract

The CuI-catalyzed intramolecular oxa-DielsAlder reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes as unactivated terminal alkynes with 4-hydroxy-6-methyl-2H-pyran-2-one is described. The reaction proceeds with remarkable chemoselectivity to yield pyranones 3 (Scheme 1). A theoretical investigation of the reaction in terms of HOMOLUMO interactions in the gas phase is also reported. The reaction could be regarded as an inverse-electron-demand DielsAlder cycloaddition. The theoretical results are in high agreement with the experimental evidences.

Keywords

, The CuI, catalyzed intramolecular oxa, DielsAlder reaction of 2, (prop, 2, yn, 1, yloxy)benzaldehydes as unactivated terminal alkynes with 4, hydroxy, 6, methyl, 2H, pyran, 2, one is described. The reaction proceeds with remarkable chemoselectivity to yield pyranones 3 (Scheme 1).