Boron Trifluoride Mediated Ring-Opening Reactions of trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates. Synthesis of Aroylmethylidene Malonates as Potential Building Blocks for Heterocycles

Thangavel Selvi and Kannupal Srinivasan*

*School of Chemistry, Bharathidasan University, Tiruchirappalli-620 024, Tamil Nadu, India, Email: srinivasankbdu.ac.in

T. Selvi, K. Srinivasan, J. Org. Chem., 2014, 79, 3653-3658.

DOI: 10.1021/jo402848v

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Abstract

trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates undergo ring-opening rearrangement and the Nef reaction in the presence of BF₃·OEt₂ to give aroylmethylidene malonates. The products are potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.

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Key Words

Cyclopropanes, Enones (Hydrolysis, Rearrangement), Nef reaction

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ID: J42-Y2014