(E)-N-methyl-1-(methylthio)-2-nitroethenamine (NMSM) 1 is a versatile molecule that contains four active sites with three functional groups on an ethane motif. NMSM as a precursor reactant has been widely applied in the diversity-oriented synthesis of various heterocyclic motifs, bis-heterocyclic, fused heterocyclic and spirocyclic scaffolds. These privileged scaffolds were synthesized via numerous types of reactions, such as Michael addition, 1,3-dipolar cycloaddition, heteroannulation reaction and also many cascade reactions via multi-component reactions. Moreover, the flexibility and high reactivity of NMSM as a versatile ambiphilic synthon signify it as a suitable building block in medicinal chemistry and bulk drug synthesis. In the present book chapter, we focused on the advances in the chemistry of NMSM as an effective reagent in organic synthesis.
Keywords: Ambiphilic synthon, Bulk drugs, Bis-heterocyclic compounds, (E)-N-methyl-1-(methylthio)-2-nitroethenamine, Fused heterocyclic compounds, Multi-component reactions, Nitroketene N, S-acetal, One-pot reactions, Spirocyclic compounds.