Synthesis Of Nitrogenous Heterocyclic Compounds Catalyzed By Solid Acid

Pollutions, especially caused by chemical industry, have become a severe problem in recent years. In order to resolve the problem, chemists have been making great efforts to achieve the environmentally friendly synthesis. Solid acid has attracted much attention for realizing this purpose due to its unique acidity, high activity and efficiency as an organic reaction catalyst. In the past decade, dihydropyrimidine derivatives have been found to be important drug potentials as the integral backbone of several calcium channel blockers, antihypertensive agents, α-1a-antagonists, and neuropeptide antagodists. Recently, the core substructure of dihydropyrimidinone-5-carboxylate was also found in several marine alkaloids with interesting biological activities. Most notably among them are the batzelladine alkaloids, which have been found to be potential HIVgp-120-CD4 inhibitors. More recently, of particular interest are reactions using carbohydrates derivatives as the aldehyde component due to the increase of the bioavailability, water solubility of the products and the generation of a new family of C–nucleoside analogues. Consequently, the synthesis of compounds containing the heterocyclic nucleus has gained importance. While Biginelli reaction is the main method of the synthesis of dihydropyrimidinones. In this paper, the recent progress of Biginelli reaction was reviewed, and further study on searching an efficient catalyst for the reaction was described. In addition, some new dihydropyrimidinone derivatives containing sugar moiety were synthesized by the three component Biginelli reaction. An efficient synthesis of 3,4-dihydropyrimidin-2-ones (DHPMs) from aldehydes, β-ketoesters and urea in ethanol solution using methanesulfonic acid (CH3SO3H) as the catalyst was described. Compared with the classical Biginelli reaction conditions, this method has the advantages of excellent yields and short reaction time. In addition, we also explored the preparation of a new kind of DHPMs containing a sugar moiety using carbohydrate aldehyde as one of the component of Biginelli reaction...