Cerium(IV) sulfate catalyzed simple and convenient synthesis of β-acetamidocarbonyl compounds

Nagarajan Panneer Selvam,Paramasivan T Perumal

doi:10.3998/ark.5550190.0010.a24

Abstract

A simple and convenient protocol for the synthesis of β-acetamido ketones has been described by one-pot three-component reaction of aromatic aldehydes and enolizable ketones or β-keto esters and acetonitrile using cerium(IV) sulfate as a catalyst. The present methodology offers several advantages such as excellent yields, non hazardous reaction condition and short reaction times.

Highlights

Multi-component reactions (MCRs) are a promising and vital field of chemistry because the synthesis of complicated molecules can be achieved in a very fast, efficient, and time saving manner without the isolation of any intermediates and it has drawn the attraction of organic chemists to develop novel multicomponent reaction.[1]
Several β-acetamido ketones/esters were synthesized as they are potential core structures for mechanism based inhibitors for various proteases
They could be converted to 1,3-amino alcohols[5] or β-amino acids, which are utilized for the synthesis of several antibiotics such as nikkomycins or neopolyoxines.[6]

Summary

Introduction

Multi-component reactions (MCRs) are a promising and vital field of chemistry because the synthesis of complicated molecules can be achieved in a very fast, efficient, and time saving manner without the isolation of any intermediates and it has drawn the attraction of organic chemists to develop novel multicomponent reaction.[1]. The reaction of substituted benzaldehydes and acetophenones with nitriles proceeded smoothly at 85 oC in the presence of 20 mol% of Ce(SO4)[2] to afford the corresponding βacetamido ketones in good yields (Scheme 1 and Table 1). Yield (%)b aAll products were characterized by Mass, IR, 1H NMR, 13C NMR and elemental analysis.

Results

Conclusion