FeCl3-DMF complex as efficient catalyst for the synthesis of 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones

F Guenadil

doi:10.4314/bcse.v33i3.18

Abstract

ABSTRACT . FeCl 3 -DMF complex has been tested on Friedel-Crafts reaction of 2(3 H )-benzoxazolone and 2(3 H )-benzothiazolone with acid chlorides and anhydrides as acylating agents. In these conditions, the 6-acyl-2(3 H )-benzoxazolones and 6-acyl-2(3 H )-benzothiazolones were obtained in yields ranging from 52 to 89%. Among the various commonly catalysts; AlCl 3 -DMF, ZnCl 2 -DMF and PPA, explored in this study, the best conditions using FeCl 3 -DMF were found the most convenient one KEY WORDS : FeCl 3 -DMF, AlCl 3 -DMF, ZnCl 2 -DMF, PPA, 6-Acyl-2(3 H )-benzothiazolones, 6-Acyl-2(3 H )-benzothiazolones Bull. Chem. Soc. Ethiop. 2019 , 33(3), 579-585. DOI: https://dx.doi.org/10.4314/bcse.v33i3.18

Highlights

The 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones derivatives, in particular are interesting, with anti-inflammatory, analgesic, antiepiliptic and antiviral properties
The ferric chloride (FeCl3) catalyst has been used as a catalyst in several organic transformations with excellent yields and great regioselectivity due to its low cost, ease of use, and environmental friendly properties [30,31,32,33,34,35,36,37,38]
It has been known that ferric chloride forms a complex with N,N-dimethylformamide by interaction with the carbonyl oxygen [39]

Summary

Introduction

The 6-acyl-2(3H)-benzoxazolones and 6-acyl-2(3H)-benzothiazolones derivatives, in particular are interesting, with anti-inflammatory, analgesic, antiepiliptic and antiviral properties. We reported the I2-N,N-dimethylformamide complex as useful catalyst in the Friedel-Crafts acylation of aromatic substrates [40]. In the work reported here, we use the ferric chloride-N,N-dimethylformamide complex (FeCl3-DMF) as a potential catalyst in the Friedel-Crafts acylation of 2(3H)-benzoxazolone and 2(3H)benzothiazolone substrates with acid chlorides and anhydrides as acylatings agents for the first time.

Results

Conclusion