Sc(OTf)3-catalyzed synthesis of polysubstituted furans from acylacetonitriles and renewable acetol

Wenbo Huang; Fang Liu; Kaimei Wang; Alexander Sidorenko; Maxim Bei; Zhigang Zhang; Wei Fang; Minghao Li; Yanlong Gu; Shaoyong Ke

Green Synthesis and Catalysis (Nov 2022)

Sc(OTf)3-catalyzed synthesis of polysubstituted furans from acylacetonitriles and renewable acetol

Wenbo Huang,
Fang Liu,
Kaimei Wang,
Alexander Sidorenko,
Maxim Bei,
Zhigang Zhang,
Wei Fang,
Minghao Li,
Yanlong Gu,
Shaoyong Ke

Affiliations

Wenbo Huang: Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China; Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, China; Corresponding author. Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China.
Fang Liu: Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
Kaimei Wang: Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
Alexander Sidorenko: Institute of Chemistry of New Materials of National Academy of Sciences of Belarus, Minsk 220141, Belarus
Maxim Bei: Institute of Chemistry of New Materials of National Academy of Sciences of Belarus, Minsk 220141, Belarus
Zhigang Zhang: Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
Wei Fang: Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China
Minghao Li: Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, China
Yanlong Gu: Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, China; School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832004, China; Corresponding author. Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, China.
Shaoyong Ke: Key Laboratory of Microbial Pesticides, Ministry of Agriculture and Rural Affairs, National Biopesticide Engineering Research Centre, Hubei Biopesticide Engineering Research Centre, Hubei Academy of Agricultural Sciences, Wuhan 430064, China; Corresponding author. Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, Wuhan 430074, China.

Journal volume & issue: Vol. 3, no. 4
pp. 380 – 384

Abstract

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A [3 + 2] cyclization reaction of acylacetonitriles and hydroxyacetone was developed by using Sc(OTf)3 as a catalyst to synthesize some furan derivatives. Bifunctional C2-based acetals, such as α-bromoacetaldehyde acetal, 1,4-dithiane-2,5-diol and glycolaldehyde diethyl acetal, also reacted readily as alternative counterpart reagents to acylacetonitriles. The established reactions can be used to synthesize a well-known fungicide, fenfuram. Antifungal activity investigation against four common plant funguses indicated that some of the obtained furan products furnish general and high biological activities.

Published in Green Synthesis and Catalysis

ISSN: 2666-5549 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-synthesis-and-catalysis/

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