One-Pot Multicomponent Synthesis of Pyrano[2,3-d]Pyrimidine Derivatives Catalyzed by Supported Magnetic Nanoparticles

Ali Maleki,Somayeh Yousefi,Abbas Ali Jafari,Vahid Eskandarpour

doi:10.3390/ecsoc-18-a041

Abstract

Heterocycles are an important class of organic compounds, because of their biological and pharmaceutical activities. It is proved that heterocycles could have more attractive and beneficial properties when they are derived by fusion with other heterocyclic rings. For example, pyrimidine is one of the useful heterocycles that exhibit useful biological activities and clinical applications; it could have additive effect in combining with other heterocycles like pyran. The significance of pyranopyrimidine is due to the occurrence of the structure in many natural products.Nowadays, multicomponent reactions (MCRs) and magnetically nanocatalysts are coming to the aim of organic synthesis to improve synthetic routes. MCRs allow the formation of several bonds in a single operation so they offer remarkable advantages such as operational simplicity, reduction in the number of workup and extraction and purification processes. Magnetically nanocatalysts are accessible from inexpensive materials and could be separated from the product without ﬁltration or centrifugation. So, magnetic separation is a green process and it avoids use of extra chemicals during the separation process. Herein, we have developed a synthetic route for one-pot three-component synthesis of annulated fused pyrano[2,3-d]pyrimidines from condensation of aromatic aldehydes, active methylene compounds and barbituric or thiobarbituric acid catalyzed by supported magnetic nanoparticles at room temperature. This efﬁcient catalyst for the preparation of biologically and pharmaceutically pyrano[2,3-d]pyrimidine derivatives includes some important aspects like the easy workup procedure, reusability of catalyst as well as high atom economy, excellent yields, and mild reaction conditions.

Highlights

Pyranopyrimidine is one of the fused heterocycles that exhibit diverse biological properties.Compounds with such annulated uracils have antitumor, antibacterial, antihypertensive, vasodilator, hepatoprotective, bronchiodilators cardiotonic, and antiallergic activities
A solution of an aldehyde 1 (1 mmol), malononitrile or ethyl cyanoacetate 2 (1 mmol), barbituric or thiobarbituric acid 3 (1 mmol) in the presence of a catalytic amount of supported metal nanoparticles was stirred at room temperature for appropriate times according to Table 1
The workup procedure of the product was easy as the nanocatalyst can be separated by an external magnet

Summary

Introduction

Pyranopyrimidine is one of the fused heterocycles that exhibit diverse biological properties.Compounds with such annulated uracils have antitumor, antibacterial, antihypertensive, vasodilator, hepatoprotective, bronchiodilators cardiotonic, and antiallergic activities. New routes for the synthesis of these molecules have attracted considerable attention in the search for a rapid entry to these heterocycles [1,2]. One-pot multicomponent reactions of aromatic aldehyde, active methylene compounds and barbituric or thiobarbituric acid has produced pyrano[2,3-d]pyrimidines in the presence of a few catalysts.

Results

Conclusion