Phenylphosphonic Acid (PPA) as an EfficientCatalyst for Synthesis of Symmetry and AsymmetryFormamidines

Publish Year: 1395
نوع سند: مقاله ژورنالی
زبان: English
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شناسه ملی سند علمی:

JR_FOCS-2-1_003

تاریخ نمایه سازی: 28 شهریور 1395

Abstract:

Introduction: Formamidines are derivatives of the unstable imidic acid having a uniqueand fascinating spectrum of biological and pharmacological activity. The aim of thepresent study id to evaluate the phenylphosphonic acid (PPA) as a catalyst for synthesis ofsymmetry and asymmetry formamidines.Method: A solution of the aniline (0.094 g, 1.0 mmol) and trimethyl orthoformate (0.318g, 3.0 mmol) in 2.5 mL water as solvent and phenylphosphonic acid (0.015 g, 10 mol%)was heat to 55 oC with natural condition for 15 min. After an appropriate time (TLC) thereaction mixture was washed with cold water, and the product was isolated by filtering. Asolution of the aniline (0.094 g, 1.0 mmol, 1 equiv) and DMF-DMA (0.360 g, 3 mmol)in solvent-free condition and phenylphosphonic acid (0.015 g, 10 mol%) was heat to 55oC with natural condition until completion (TLC). The reaction was cooled to roomtemperature, and after addition water to the reaction, the product as colorlessoil wasextracted by CH2Cl2.Result: We had found that both Amberlist-15 and phenylphosphonic acid(PPA) areeffective in reaction progress in 45 and 10 min, respectively. But, based on quick reactiontime and also easy water separable of the formamidine from water soluble phenylphosphonicacid (PPA), we select PPA as ideal catalyst in synthesis of N, N-diarylformamidine.Conclusion: The reaction of alkyl orthoformates with aromatic amines in the presenceof phenylphosphonic Acid (PPA) as a catalyst to produce alkyl N, N-disubstitutedFormamidines has been shown to be general. Reaction of orthoformates with an aromaticprimary-amine, preferably in the presence of PPA in solvent-free or water-mediumcondition, gives formamidine in excellent yields.

Authors

Maede Valizadeh

Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran,Babolsar, Iran

Mahmood Tajbakhsh

Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran,Babolsar, Iran