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Synthesis 1997; 1997(12): 1489-1494
DOI: 10.1055/s-1997-1376
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Convenient Synthesis of Fluoroalkyl-Substituted Heterocycles from 1-Fluoroalkyl-2-iodoalkenes

Hui-Ping Guan, Xiao-Qing Tang, Bing-Hao Luo, Chang-Ming Hu*
  • *354 Fenglin Road, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China, Fax +86(21)64166128
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Publication Date:
31 December 2000 (online)

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A convenient synthesis of fluoroalkyl-substituted heterocycles including 3-trifluoromethylpyrazoles 7, 5-trifluoromethylisoxazoles 8 and 4-trifluoromethylpyrimidines 9 is described. This two-step sequence consists of a radical addition of fluoroalkyl iodides 1 to alkynes 2 to afford the corresponding alkenes 3 and condensation of 3 with hydrazine, hydroxylamine or amidines to give the afore-mentioned heterocycles, respectively. A possible pathway is suggested.

radical addition - condensation - fluoroalkyl-substituted heterocycles - 1-fluoroalkyl-2-iodoalkenes - hydroxylamine - amidines