Synthesis 2019; 51(18): 3520-3528
DOI: 10.1055/s-0037-1611871
paper
© Georg Thieme Verlag Stuttgart · New York

Preparation of Imidazole Derivatives via Bisfunctionalization of Alkynes Catalyzed by Ruthenium Carbonyl

Yi-tong Ruan
a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China   Email: heling2012@scu.edu.cn
,
Yue-peng Chen
a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China   Email: heling2012@scu.edu.cn
,
Ling-hui Gu
a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China   Email: heling2012@scu.edu.cn
b   Antibiotics Research and Re-evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu, 610052, P. R. of China
,
Yang Luo
a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China   Email: heling2012@scu.edu.cn
,
Ze Yang
a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China   Email: heling2012@scu.edu.cn
,
Ling He
a   Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, Sichuan, 610041, P. R. of China   Email: heling2012@scu.edu.cn
› Author Affiliations
We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21072131) and Sichuan University–Lu Zhou Strategic Cooperation Projects (No. 2017 CDLZ-S34)
Further Information

Publication History

Received: 13 December 2018

Accepted after revision: 31 May 2019

Publication Date:
26 June 2019 (online)


Abstract

A one-step, oxidative bisfunctionalization of alkynes to generate cis-enediol diacetates catalyzed by ruthenium carbonyl (triruthenium dodecacarbonyl) is presented. The reaction was performed using the alkyne, (diacetoxyiodo)benzene, Ru3(CO)12 as the catalyst, and toluene as the solvent at 100 °C to give the cis-enediol diacetates in up to 82% yields. This method overcomes the shortcomings of existing methods, such as tedious reaction steps, substrate limitations, and the use of toxic reagents. Furthermore, the reaction of module cis-enediol diacetates with ammonium carbonate [(NH4)2CO3] in an alcohol solvent gave imidazole derivatives in 37–84% yields, thus providing a simple and mild new method for the synthesis of imidazole compounds.

Supporting Information

 
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