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A Microwave-Promoted/Assisted Method for Rapid Preparation of Biaryl Seven-membered Lactones

[ Vol. 13 , Issue. 3 ]

Author(s):

Chunqi Hu, Jun Li and Wenting Du   Pages 301 - 305 ( 5 )

Abstract:


Background: Biaryl seven-membered lactones (BSLs), the target compounds are a class of bioactive compounds with anti-arrhythmic activity, which also serve as a starting material or structural units for chemical synthesis.

Objective: To report a simple and efficient procedure for the synthesis of biaryl seven-membered lactones.

Method: Under microwave, the umpolung reaction was promoted by N-heterocyclic carbenes under oxygen, with anhydrous potassium carbonate as base and with 1,4,7,10,13,16-Hexanoxacyclooctadecane (18-crown-6) as a phase-transfer catalyst.

Results: The practical protocol was found to be compatible with different structurally diverse substrates and with moderate to excellent yields.

Conclusion: This synthesis method has the advantage of high efficacy and novelty, short reaction time, operation simplicity, mild condition and high yields, providing a useful and atom-economic approach to the synthesis of BSLs.

Keywords:

BSLs, carbene salt, lactones, N-heterocyclic carbine, microwave, umpolung reaction.

Affiliation:

College of Chemistry & Chemical Engineering, Shaoxing University, Shaoxing 312000, Department of Pharmacy, Hangzhou Medical College, 481 Binwen Road, Hangzhou 310053, Department of Pharmacy, Hangzhou Medical College, 481 Binwen Road, Hangzhou 310053, China; Wenzhou Medical University, Wenzhou 325035

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