Synthesis and characterization of some novel 4-furyl substituted 3-imidazoline 3-oxides

Özden Özel Güven

doi:10.3998/ark.5550190.0008.f14

Abstract

Novel 4-furyl substituted 3-imidazoline 3-oxides were synthesized by the reaction of 2-bromo-1- (2-furanyl)ethanone oxime with aromatic amines and aldehydes, including formaldehyde, using one pot procedures involving the reactions of in situ formed α-amino oximes with aldehydes and also by one pot procedures involving the reactions of in situ formed imines with α-halo oximes.

Highlights

Cyclic nitrones, which are heterocyclic compounds containing an azomethine N-oxide group, have a wide range of synthetic potentialities.[1]
The synthesis of 1,4-diaryl and 1,2,4-triaryl imidazoline 3-oxides containing a phenyl ring as aryl groups have been reported6a-d and these N-oxides have been used as dipoles in [3+2] cycloaddition reactions with various dipolarophiles to obtain biologically important isoxazolidine and isoxazoline rings.7a-f
The methods that were used in this study are easy and short to synthesize potentially biologically active compounds

Summary

Introduction

Cyclic nitrones, which are heterocyclic compounds containing an azomethine N-oxide group, have a wide range of synthetic potentialities.[1]. The ability of the nitrones to undergo 1,3- and 1,4cycloaddition reactions makes it possible to use them in the synthesis of various heterocyclic systems, including natural compounds.[3,4]. There is no data about the 4-furyl substituted 3-imidazoline 3-oxides in the literature. A series of novel 4-furyl substituted 3-imidazoline 3-oxides have been synthesized and will be used as dipoles in [3+2] cycloaddition reactions in forthcoming studies because of the importance of the furan ring. As one of the representative five-membered heterocycles, is found in many naturally occurring compounds.[8] Besides this, oxidation of furan rings gives useful intermediates for the synthesis of new compounds.[9,10]

Results and Discussion

R1NH2 5

Conclusions