An Efficient Greener Approach for N-Acylation of Amines in Water Using Benzotriazole Chemistry.

Tarek S Ibrahim,Siva S Panda,Nabil A Alhakamy,Israa A Seliem,Mohamed Elagawany,Zakaria K M Abdel-Samii,Amany M M Al-Mahmoudy,Hani Z Asfour

doi:10.3390/molecules25112501

Abstract

A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.

Highlights

N-Acylation reactions are widely used in the organic chemistry, biology, pharmaceutical and agricultural industries [1,2,3]
We extend the efficient synthetic protocol for the N-acylation of amines, which could be an important tool for conjugate chemistry and for the synthesis of 2-substituted benzimidazoles without any catalyst, organic solvent or additional reagent
Several methods have been reported for arylamides, including the use of enzymes and flow chemistry [57,58,59,60,61,62,63,64,65,66,67,68,69,70,71], and we believe we are reporting, for the first time, the synthesis of amino acid arylamides in water

Summary

Introduction

N-Acylation reactions are widely used in the organic chemistry, biology, pharmaceutical and agricultural industries [1,2,3]. They are a straightforward and powerful tool for the protection of amino groups in multistep organic syntheses, for their convenient activation towards further chemical transformations, or as widespread amide building blocks in biologically active targets, natural products and pharmaceuticals [4,5]. Most of the natural products and clinically used drugs contain an amide bond [9,10,11,12,13,14].

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Results

Conclusion