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ZnO Catalyzed Efficient Synthesis of Some New 2-Substituted-4,6-diarylpyrimidines

DOI: 10.5402/2012/242569

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Abstract:

A simple and efficient protocol is developed for the synthesis of 2-substituted-4,6-diarylpyrimidines from one-pot three-component reaction of 4′-hydroxy-3′,5′-dinitro substituted chalcones, S-benzylthiouronium chloride (SBT), and heterocyclic secondary amines (morpholine/pyrrolidine/piperidine) in the presence of 15 mol% of ZnO as a heterogeneous catalyst. The present methodology offers several advantages such as being a simple procedure as well as providing excellent yields, and short reaction time. The catalyst is inexpensive, stable, and can be easily recycled and reused for several cycles with consistent activity. 1. Introduction Since many decades, bioactive heterocyclic compounds are one of the main topics of interest for the medicinal chemists as it displays a number of pharmacological activities. Nitrogen, sulphur, and oxygen containing five- and six-membered heterocyclic compounds have occupied enormous significance in the field of medicinal chemistry. The multicomponent reactions (MCRs) have emerged as an efficient and powerful tool in modern synthetic organic chemistry allowing the facile creation of several new bonds in a one-pot reaction. Therefore, in the last decade, research in academia and industry has increasingly emphasized the use of MCRs as well as domino reaction sequences for a broad range of products [1, 2]. Due to the atom economy, convergent character, and simplicity of one-pot procedures, multicomponent condensation reactions (MCRs) have an advantageous position among other reactions. The discovery and development of novel MCRs is receiving a growing interest from industrial chemistry research groups and represents a new challenge for organic chemists and to the basic understanding of organic chemistry itself [3]. Recently, intensive studies have been focused on the development of catalytic systems owing to their importance in synthetic organic chemistry. One of the most attractive synthetic strategies favoured by organic chemists is the use of heterogeneous catalyst in increasing the efficiency of a wide range of organic synthesis. Heterogeneous catalysis is being used in the fine chemical industries because of the need for more environmental friendly production technology. This tendency is assisted by the availability of catalytic materials and modern techniques of creating and investigating specific active sites on catalyst surfaces [4, 5]. Metal oxides exhibit both Lewis acid and Lewis base character at their surface [6]. The basic skeleton of chalcones possesses an α, β-unsaturated carbonyl group, used as the starting

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