A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates |
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Authors: | Haizhen Jiang Lan Sun Shijie Yuan Wenjun Lu Wen Wan Shizheng Zhu Jian Hao |
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Institution: | 1. Department of Chemistry, Shanghai University, Shanghai 200444, China;2. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China |
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Abstract: | A facile one-pot procedure has been developed for the synthesis of 1,3-imidazolines and 1,3-oxazolines bearing fluorinated alkyl groups at the 2-position. The reaction involves the condensation of N-monosubstituted ethane-1,2-diamines or 2-aminoethanols with a fluorinated carboxylic acid in the presence of PPh3/CX4. The proposed mechanism is that the amide intermediates were initially formed, and then converted to the imidoyl halide intermediates in the presence of PPh3/CX4, followed by rapid intramolecular cyclization to 1,3-diazoline products. This protocol allows for the synthesis of 2-bromodifluoromethyl-1,3-imidazoline, a useful CF2Br-heterocyclic building block, which can be used for the synthesis of gem-difluoromethylene linked compounds. |
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