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 (free Supporting Information)
see article for more reactions
trans-2-Aryl-3-nitro-cyclopropane-1,1-dicarboxylates undergo ring-opening rearrangement and the Nef reaction in the presence of BF3ˇOEt2 to give aroylmethylidene malonates. The products are potential precursors for heterocycles, such as imidazoles, quinoxalines, and benzo[1,4]thiazines.
see article for more examples