Synthesis of some new heterocyclic compounds derived from 2-Chloro-3-formyl quinoline

Ala Ayoob,Fatma Mohmood

doi:10.33899/edusj.2013.163057

Abstract

In this paper the Synthesis of some substituted 2-Chloro-3-formyl quinoline (2a–d) by treating various substituted acetanilide or 1-(4-substituted phenyl) ethanone oxime with POCl3 in dimethyl formamide. It proceeds through Vilsmeier – Haack cyclization. The condensation of 2-chloro-3-formylquinoline with p-Hydroxyacetophenone, 2-acetyl pyridine, 2-acetyl furan or 3-acetyl indole via Claisene– Schmiatcondensations gives quinolinylchalcone (4a – d). Newpyrazoline derivatives were synthesized by condensing the appropriate chalcone (4a) with hydrazine hydrate or phenylhydrazine (10 – 11). Oxazole (12) is reported from compound (4a) and hydroxyl amine hydrochloride is in basic medium. The reaction of chalcone (4a) with urea, thiourea or quinidine hydrochloride gives pyrimidine-2-one (7), pyrimidine-2-thiol (8) or 2- amino pyrimidine (9) respectively.Oxirane (6) prepared from reaction of chalcone (4a) with hydrogen peroxide in basic medium. The reaction of chalcone (4a) with bromine gives dibromide (5). The structures of synthesized compounds were confirmed by spectral and physical methods.

Highlights

Quinoline, known as L-azanaphthalene, 1-benzaine or benzo(b)pyridine is an aromatic nitrogen compound characterized by a double ring structure contain a benzene fused pyridine at two adjacent carbon
Several quinoline derivatives isolated from natural resources or prepared synthetically are significant with respect to medicinal chemistry and biomedical use
Quinoline derivatives are some of the oldest compounds which have been utilized for the treatment of a variety of disease.The bark of the cinchona plant containing quinine was utilized to treat palpitations [12]

Summary

INTRODUCTION

Known as L-azanaphthalene, 1-benzaine or benzo(b)pyridine is an aromatic nitrogen compound characterized by a double ring structure contain a benzene fused pyridine at two adjacent carbon. The plant family have been known to be the rich source of quinoline alkaloids [10], pyranoquinoline alkaloids gained importance due to their several pharmacological activities like anticoagulant [11]. Several quinoline derivatives isolated from natural resources or prepared synthetically are significant with respect to medicinal chemistry and biomedical use. Quinoline derivatives are some of the oldest compounds which have been utilized for the treatment of a variety of disease.The bark of the cinchona plant containing quinine was utilized to treat palpitations [12]. There are many methods available for functionalized quinolines the Vilsmeier approach is found to be among the most efficient for achieving useful transformations and hetero annulations, 2-chloro-3-formyl quinoline the primary intermediate, is a good starting material for the preparation of different quinoline derivatives

MATERIALS AND METHODS

RESULTS AND DISCUSSION

C O P Cl