Studies On Synthesis Methods Of Imidazoline And Imidazole Compounds

Nitrogen-containing heterocyclic compounds have been widely used and their synthesis has been widely concerned by researchers.In this paper,the synthesis methods of imidazoline and imidazoline compounds are reviewed.The full text includes the following six chapters:Chapter 1:Research progress on synthesis methods of imidazoline compoundsImidazoline compounds play an important role in natural products,coordination chemistry,medicinal chemistry,organic synthesis and homogeneous catalysis.This chapter mainly introduced the research progress of the synthesis of imidazoline compounds from different raw materials(1,2-diamines,isonitrile,amidines,imines,azacyclic propane,nitrile,amides,etc.)in recent years,and the application of imidazoline compounds in some important organic reactions(Friedel-Crafts reaction,Diels-Alder reaction,Henry reaction,Morita-Baylis-Hillman reaction,etc.).Chapter 2:Research progress on synthesis methods of imidazole compoundsImidazole is one of the important heterocyclic compounds containing two nitrogen.Due to its unique structural characteristics and excellent electron-rich properties,imidazole heterocyclic compounds are widely used in organic synthesis,natural products,pharmaceutical chemistry and other fields.This chapter mainly introduced the recent progress in the synthesis of imidazole compounds from different materials(ketones,alkynes,amidines,nitrile or isonitrile,amines,acyl chloride and imines,etc.).Chapter 3:Acid-mediated the synthesis of imidazoline from three-component cyclization of amidines,sulfoxonium ylides and benzaldehydesIn this chapter,an efficient acid-mediated three-component reaction for the synthesis of tetra-substituted imidazoline is introduced.This reaction used simple amidine,sulfoxonium ylides and benzaldehyde as raw materials,avoiding the pre-functional group of raw materials,without metal catalyst,and had the advantages of high regional selectivity and high atomic utilization rate.This method could synthesize imidazoline derivatives of various functional groups with high yield under mild reaction conditions,which provided a practical method for the synthesis of tetra-substituted imidazoline.Chapter 4:Selective synthesis of trisubstituted imidazole by I₂-catalyzed[3+2]cycloadditionsIn this chapter,we mainly introduced a method to construct two different substituted imidazole by iodine-catalyzed[3+2]cycloaddition reaction.By controlling one of the reaction materials,we selectively synthesized two imidazole compounds substituted in different positions.In the presence of I₂/TEMPO,we synthesized 1,2,4-trisubstituted imidazole using amidine and propiophenone as raw materials,and 1,2,5-trisubstituted imidazole was synthesized using amidine and enamine ketone as raw materials in the presence of Fe Cl₃·6H₂O/I₂.It provided a simple method for the synthesis of multi-substituted imidazole compounds.Chapter 5:Copper/iodine-catalyzed[3+2]cycloaddition of amidine with acrylate for imidazole synthesisIn this chapter,we mainly introduced a highly efficient method of synthesis of 1,2,4-trisubstituted imidazoles by[3+2]cycloaddition of amidine and acrylate by copper/iodine-catalyzed.This method could be used to prepare trisubstituted imidazole derivatives with moderate to good yield using inexpensive catalysts(copper/iodine)from simple raw materials,providing a simple and convenient way for the synthesis of 1,2,4-trisubstituted imidazole derivatives.Chapter 6:Selective synthesis of(1H-benzo[d]imidazol-2-yl)(phenyl)-methanone and quinoxaline from aromatic aldehyde and o-phenylenediamineIn this chapter,we designed a method for the selective synthesis of(1H-benzo[d]imidazole-2-yl)(phenyl)methanone and quinoxaline from o-phenylenediamine and phenylacetaldehyde.In the presence of N,N-dimethylformamide/sulfur,we obtained(1H-benzo[d]imidazole-2-yl)(phenyl)methanone from o-phenylenediamine and phenylacetaldehyde.In 1,4-dioxane we have obtained quinoxaline derivatives.In this reaction,a new C-N bond is constructed,which provides a simple and economical way for the synthesis of 1H-benzo[d]imidazole-2-yl)(phenyl)methanone and quinoxaline.