Synthesis Of Trifluoromethylthioenamine, Benzofuran And 1,2,3-triazoles

Organic fluorinated compounds,1,2,3-triazole and benzofuran derivatives are three kinds of compounds with wide biological activity.Among the fluorinated functional groups,because-SCF3 has strong electronegativity,hydrophobicity and strong C-F bond energy,the compounds containing-SCF3 have many biological activities,such as anti-tumor,anti-inflammatory,and the compounds containing-SCF3 have wide application prospects in the fields of agricultural chemistry,medicine.At present,the study on the introduction of trifluoromethylthio into the molecule has become a new hotspots in organic fluorine chemistry.1,2,3-triazole and benzofuran derivatives are two important nitrogen and oxygen-containing heterocyclic compounds,which are widely found in natural productss and possessed a variety of biological activities,such as anti-HIV,anti-psychosis,etc.At present,many drugs on the market contain these two kinds of heterocyclic framework.Therefore,it is a feasible strategy to synthesize 1,2,3-triazole and benzofuran compounds by organic synthesis.In this paper,a simple and efficient synthesis method of these three kinds of heterocyclic compounds has been developed by reference to the literature.In chapter 1,the research progress of trifluoromethylation,1,2,3-triazole derivatives and benzofuran derivatives is briefly reviewed.In chapter 2,a series of trifluoromethyl compounds were synthesized from the trifluoromethylation of heterocyclic ketolamine(HKAs),1,1-enediamine,enaminones at room temperature for 30 min,using acetonitrile as solvent,and the yield was 86%93%.In chapter 3,an experimental method for the synthesis of 2-aminobenzofuran derivatives from 1,1-endiamine,α,β-unsaturated ketones were established.The method was heated for 4 hours with 1,4-dioxane as solvent,HAc as catalyst,and the 332-aminobenzofuran derivatives were successfully synthesized with a yield of 79%89%.In Chapter 4,I have completed the synthesis of 25 1,2,3-triazole derivatives and designed an experimental method for the synthesis of 1,2,3-triazole using 1,1-endiamine and TsN3 as raw materials,using 1,4-Dioxane as solvent and heated for 3 hours,the yield of 55%-92%.All derivatives containing-SCF3 enamine,benzofuran were characterized by NMR,MS,IR and so on.and single crystal culture and determination of compound 3-11 and 9b were carried out.