Synthesis of Difluoromethylene-Containing 1,2,4-Oxadiazole Compounds via the Reaction of 5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole with Unsaturated Compounds Initiated by Sodium Dithionite

Xueyan Yang; Zhonghua Wang; Xiang Fang; Xianjin Yang; Fanhong Wu; Yongjia Shen

doi:10.1055/s-2007-983705

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Synthesis 2007(12): 1768-1778
DOI: 10.1055/s-2007-983705

PAPER

Synthesis of Difluoromethylene-Containing 1,2,4-Oxadiazole Compounds via the Reaction of 5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole with Unsaturated Compounds Initiated by Sodium Dithionite

Xueyan Yang^a, Zhonghua Wang^a, Xiang Fang^a, Xianjin Yang^a, Fanhong Wu*^a,b, Yongjia Shen^a
^a Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, P. R. of China
^b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Rd, Shanghai 200032, P. R. of China
Fax: +86(21)64253074; e-Mail: wfh@ecust.edu.cn;

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Publication History

Received 28 February 2007
Publication Date:
08 June 2007 (online)

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Abstract

5-(Difluoroiodomethyl)-3-phenyl-1,2,4-oxadiazole, synthesized by the iodination of the corresponding zinc reagent of 5-(bromodifluoromethyl)-3-phenyl-1,2,4-oxadiazole, reacted with various unsaturated compounds, such as alkenes, alkynes, pent-4-en-1-ols, and pent-4-enoic acids, in the presence of sodium dithionite and sodium hydrogen carbonate in aqueous acetonitrile solution at ambient temperature to afford various difluoromethylenated 1,2,4-oxadiazole-containing compounds, including γ-butyrolactones and tetrahydrofurans, in moderate yields.

Key words

difluoromethylene - 1,2,4-oxadiazole - γ-butyrolactone - addition - cyclization

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