Abstract
A green, simple and highly efficient synthesis of N,N-diarylsubstituted formamidines has been developed employs reaction of triethylorthoformate (TEO) with aromatic amines catalyzed by cerium (IV) ammonium nitrate (CAN) in water at ambient temperature. This method offers the advantages of proceeding under environmentally friendly technique with high yields and simplicity either in conducting the reaction or handling the products.
Highlights
Formamidines are of considerable interest in fields related to organic and medicinal chemistry
In continuation to our efforts utilizing a simple and green technologies for organic synthesis [30] we reported for the first time, a convenient, green, highly efficient synthesis of N,N--diarylsubstituted formamidines in water at ambient temperature performing cerium (IV) ammonium nitrate (CAN) in catalytic amount
With the aim of optimizing experimental conditions, we initially explored the reaction of aniline (1a) (1 mol) and triethylorthoformate (2) (1 mol) in water (20 mL) in the presence of CAN (10 mol%) at ambient temperature (27 ̊C)
Summary
Formamidines are of considerable interest in fields related to organic and medicinal chemistry. The exchange of N,N-dimethylformamidines or acetamidines by a variety of amines has been reported to be the most popular method for the synthesis of symmetrical and unsymmetrical formamidines [21] This approach suffers from drawbacks of high temperatures and the use of protic organic solvents (mostly methanol or ethanol) for a period of 1 - 48 hours [22]. A revisiting of the effect of acid in the amine exchange of N,N-dimethylformamidines has been recently reported [18] which allowing the preparation of highly electron-rich compounds that are difficult to obtain under standard conditions. In continuation to our efforts utilizing a simple and green technologies for organic synthesis [30] we reported for the first time, a convenient, green, highly efficient synthesis of N,N--diarylsubstituted formamidines in water at ambient temperature performing CAN in catalytic amount
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