The Research On The Synthesis Of Multisubstituted Furans, Pyrroles And Hexatomic Ring Compounds Via In-catalyzed

In contrast to the conventional Lewis acid, In(â…¢) compounds have some merit such as being able to bear water, high-effect, excellent selectivity. There are able to boost various organic reaction proceed under mild condition effectively demonstrating the fine application prospect. Using Indium salts as catalyst to be paid more attention because of the cheap price of Indium and their environmental friendliness. In this paper a series of reactions promoted by Indium salt were studied. The work we have done are displayed:First, for synthesis the necessary pioneer compounds, Iron trichloride Catalyzed Propargylation of 1,3-Dicarbonyl compounds was studied. The studying results indicated that Iron trichloride catalyzed electrophilic addition of propargylic alcohols with 1,3-dicarbonyl compounds in 1,2-dichloroethane heated to reflux for 8h under nitrogen atmosphere to give the relative target compound was developed, the yield was 80.9～94.2﹪. Propargylation of 1,3-dicarbonyl compounds was realized by Lewis acid catalysis.Secend, the synthesis of furans has always been an area of intensive research by synthetic chemists due to their wide presence in a variety of natural products and pharmaceuticals. In the past methods the preparation of furans needs advanced starting material such as alkynones and allenones, and needs noble metal as catalyst, so it couldn't apply in large scale. In summary, we have developed an efficient protocol for the synthesis of tetrasubstituted furans from propargylic alcohols and 1,3-dicarbonyl compounds. The success of the method depended on the use of InCl₃ as catalyst. Our reaction compares favorably with the reported method in terms of both the product yields and operational simplicity. Our method uses only a catalytic amount of InCl₃, requiring no stop during the middle of the reaction and it also does not require the addition of stoichiometric amount of base to effect the cyclization step. One pot synthesis of furans have come true really.Third, the pyrroles are a kind of important heterocycle compounds having important use in fields such as medicine, food, fine chemicals, macromolecular material. In the recent report about the synthesis of pyrroles all need the noble metal as catalyst. In this paper, the multisubstituted pyrroles were synthesized from 2-propynyl-1,3-dicarbonyl compounds derivatives react with amines via InCl₃ catalyzed. This method provided guarantee to get pyrroles in large scale.Forth, Intramolecular hydroarylation is a form addition of arene C-H bonds across multiple bonds in an intramolecular manner. In contrast to the intermolecular version, only a handful of examples have surfaced regarding transition metal-catalyzed intramoleculer hydroarylation of alkenes. Intramoleculer hydroarylation promoted by mild and excellent catalyst is always the hot spot studying. In this paper, several common, commercially available indium and iron salts were screened as catalysts. Results indicated that the annulated product could be obtained by In(OTf)₃ catalyzed in dichloroethane, it established a basis for application of this reaction in large scale.From above study, one side extending the breadth of In-catalysis, others providing the new and excellent methods for the synthesis of furans, pyrroles and hexatomic ring compounds.