Tetrahedron 2018-03-07

Proton transfer process in synthesis of 3-acetyl-4-(substituted ethylenyl)coumarins and chromeno[3,4-c]pyridines

Abdolali Alizadeh, Reza Mohammadi, Fahimeh Bayat, Long-Guan Zhu

Index: 10.1016/j.tet.2018.03.015

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Abstract

The triphenylphosphine mediated reactions of electron-deficient carbon-carbon triple bonds with 3-acetylcoumarins in dichloromethane afford functionalized 3-acetyl-4-(substituted ethylenyl)coumarins. Also, triphenylphosphine-catalyzed three-component cascade annulation reactions of 3-acetylcoumarins, activated acetylenic compounds, and hydrazines or amines provide a straightforward access to 3,5-dihydro-2H-chromeno[3,4-c]pyridine-1,2-dicarboxylates. In these strategies, the main step to the target products is proton transfer process. All products were obtained in good to high yields.

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