Reaction Of 4-Trifluoromethyl-p-Quinols With Alkyne And Its Application In Synthesis Of Furan Derivatives

Furan and its derivatives are an important class of aromatic heterocyclic compounds,which are widely presented in pharmaceuticals and natural products with have good biological activities.Therefore,the synthesis of furan and its derivatives has attracted attentions.It can be synthesized by reactions such as intramolecular or intermolecular oxidative cyclization.A catalyst such as a transition metal or a Lewis acid is often required in the reactions.In the reaction,there are many problems such as harsh reaction conditions and expensive reagents.The development of concise and efficient synthesis methods of furan derivatives still has a good application prospect.p-Quinols compounds are important aromatic precursors with multiple reaction sites and are simple and practical intermediates in organic synthesis.Our research group synthesized a series of polysubstituted aromatic hydrocarbons from p-quinols.Based on the previous research work,combined with the recently reported reuse of propargyl alcohol compounds in the synthesis of furan derivatives,the addition reaction of p-quinols with acetylene and its application in the synthesis of furan derivatives were systematically studied.A series of benzofuran derivatives were synthesized in a high yield by a highly efficient series cyclization reaction through an olefinic intermediate.The reaction has the advantages of mild reaction conditions,no need of anhydrous and anaerobic operation,short reaction time,high yield and wide range of reactants.In this paper,27 new compounds were successfully synthesized,and the products were charaterized by experiments such as ¹H-NMR,¹³C-NMR,high resolution mass spectrometry,gas-mass chromatography and single crystal X-ray diffraction.