2,5-Dimethoxy-Beta-Nitrostyrene, also known as 2,5-二甲氧基-β-硝基苯乙烯, is an unsaturated nitro compound with high chemical reactivity due to the electron-withdrawing nature of the nitro group on the double bond in its structure. It is commonly used as an organic synthesis intermediate and has applications in organic chemistry research and the synthesis of nitrogen-containing active molecules, such as triazole bioactive molecules.

Chemical Properties

The chemical reactivity of 2,5-Dimethoxy-Beta-Nitrostyrene is mainly focused on the double bond unit in its structure, which exhibits some electrophilicity due to the strong electron-withdrawing nature of the nitro group. It can undergo Michael addition reactions with common nucleophilic reagents such as organic alcohols or amine compounds to yield corresponding alkyl nitro derivatives. Additionally, 2,5-Dimethoxy-Beta-Nitrostyrene can undergo reduction reactions to produce amine derivatives under the action of reducing agents.

Condensation Cyclization Reaction

Figure 1: Condensation Cyclization Reaction of 2,5-Dimethoxy-Beta-Nitrostyrene

To carry out the condensation cyclization reaction of 2,5-Dimethoxy-Beta-Nitrostyrene, dissolve 2,5-Dimethoxy-Beta-Nitrostyrene (1.5 mmol) and NaN3 (2.25 mmol) in dry DMF (15 mL) in a dry reaction flask. Slowly add p-toluenesulfonic acid (0.75 mmol) to the reaction mixture under stirring conditions. Stir the reaction mixture at 60°C in air for 1-3 hours. Monitor the reaction progress by TLC plate. After the reaction is complete, cool the reaction mixture to room temperature, quench it with water (50 mL), and extract the reaction mixture three times with ethyl acetate (3×50 mL). Separate the organic layer, dry it over anhydrous Na2SO4, filter off the drying agent, and evaporate the filtrate under vacuum. Purify the residue by column chromatography on silica gel (EtOAc/hexane) to obtain the target product molecule.

Chemical Applications

2,5-Dimethoxy-Beta-Nitrostyrene is primarily used as an organic synthesis intermediate and has been reported to be used in the preparation of tyrosine-specific protein kinase inhibitors.

References

[1] Bhagat, Ujjawal Kumar; et al Tetrahedron Letters 2017,58,298-301.