An Efficient FeCl&amp;lt;sub&amp;gt;3&amp;lt;/sub&amp;gt; Catalyzed Synthesis of N,N’-Diarylformamidines

Pushkin Chakraborty,Subhas C Roy

doi:10.4236/gsc.2013.31005

Abstract

An efficient FeCl3 catalyzed synthesis of N,N’-diarylformamidines using triethylorthoformate (1 equivalent) and primary aryl amines (2 equivalents) at ambient temperature has been described. This methodology provides an eco-friendly and simple procedure without using any hazardous and expensive chemicals.

Highlights

Formamidines have structural similarity to the imidazole ring, a part of the histamine molecule, are supposed to possess enormous biological activities
Sadek et al [26] reported the synthesis of diarylformamidines using ceric ammonium nitrate (CAN) in water
It is well known that CAN is a toxic and strong oxidizing reagent and especially in water it shows strong acidic property to affect many sensitive functional groups

Summary

Introduction

Formamidines have structural similarity to the imidazole ring, a part of the histamine molecule, are supposed to possess enormous biological activities. The biochemical aims of formamidines include monoamine oxidase inhibitor [1,2], adrenergic, neurochemical receptors [3,4,5,6,7,8] and prostaglandin E2 synthesis [9]. Formamidines are noted for their complexation with transition metals [10,11] and usage as auxiliaries in asymmetric synthesis [12,13], electrophiles [14]. The utility of formamidines as support linkers in solid phase synthesis [15] is well established in the field of organic synthesis. Formamidines are vastly used for the preparation of imidazolium salts which are the precursor for the synthesis of N-Heterocyclic carbenes [16]. There have been reported some cryoscopic molecular weight determination experiments utilizing the molecular association property of diarylformamidines in benzene solution [18]

Results and Discussion

Conclusion

General Procedures

Representative Procedure for the Synthesis of Diarylformamidines