41555-66-2

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 60-34-4 methylhydrazine 
• 4230-93-7 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 

Downstream Products

• 40092-23-7 C₁₄H₂₁N₃O₃ 
• 41555-79-7 3-{N'-[1-(3,4-Dimethoxy-phenyl)-meth-(E)-ylidene]-N-methyl-hydrazino}-2-methyl-cyclopent-2-enone 
• 41555-69-5 3-<2-(3,4-Dimethoxybenzyliden)-1-methylhydrazino>-2-cyclohexen-1-on 
• 40091-97-2 C₁₅H₂₃N₃O₃ 

Relevant academic research and scientific papers

Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process

In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.

Synthesis of 3-(2-nitrovinyl)-4H-chromones: Useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones

The Henry-type Barbier addition of bromonitromethane to 3-formylchromone, immediately followed by acetylation and concomitant elimination to afford nitroalkenes in excellent yield and total (E)-selectivity is described. Cycloaddition of N-methylhydrazones