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Review | Special issue | Vol 84, No. 1, 2012, pp.115-134
Published online, 28th July, 2011
DOI: 10.3987/REV-11-SR(P)3
Practically Usable C3 Building Blocks for the Syntheses of Nitro Heterocycles

Nagatoshi Nishiwaki,* Shotaro Hirao, Jun Sawayama, and Kazuhiko Saigo

*School of Science and Technology, Kochi University of Technology, Tosayamada-cho, Kochi, 782-8502, Japan


Nitromalonaldehyde (NMA-H) is one of useful synthons for synthesizing nitro compounds. However, NMA-H itself cannot be practically employed because of its unstable property. Therefore, sodium salt of NMA-H (NMA-Na) has been used as its synthetic equivalent from old time, and NMA-Na is still important even now albeit several restrictions with regard to safety and treatability. On the other hand, dinitropyridone, nitropyrimidinone and dinitropyrazole can be employed in place of NMA-Na for the same purpose, and furthermore azadienamines, formylnitroenamines and dinitropyrazole also serve as the synthetic equivalents of NMA-H, which are usable in common organic solvents with safety. These reagents condense with dinucleophiles to afford various kinds of nitro compounds.