文献类型：期刊文献

英文题名：Synthesis and substitution reactions of β-alkoxyvinyl bromodifluoromethyl ketones

作者：Fang, Xiang[2];Chen, Yang[2];He, Doming[2];Yang, Xianjin[2];Wu, Fanhong[1,2]

机构：[1]Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China;[2]E China Univ Sci & Technol, Sch Chem & Mol Engn, Lab Adv Mat & Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2008

卷号：129

期号：12

起止页码：1167

外文期刊名：JOURNAL OF FLUORINE CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000261846500007)】；

基金：This research work was supported by the National Natural Science Foundation of China (Grant No. 20672034).

语种：英文

外文关键词：Fluorinated synthons; beta-Alkoxyvinyl bromodifluoromethyl ketones; Enaminones

摘要：beta-Alkoxyvinyl bromodifluoromethyl ketones 1a, 1b and 1c were synthesized by the reaction of bromodifluoroacetic anhydride with appropriate vinyl ethers in high yields. The acyclic enone 1a reacted with amines to give the corresponding beta-aminovinyl bromodifluoromethyl ketones 2 in good yields. The reaction of la with electrophilic reagent ICI yielded alpha-iodoenone 4. The substitution reaction of the cyclic enones 1b and 1c with thio-nucleophiles gave the corresponding difluoromethylene thioethers 6. The three-component reactions of 2 with primary amines and formaldehyde gave multifunctional 1,2,3,4-tetrahydropyrimidine 3 in moderate yields. (c) 2008 Elsevier B.V. All rights reserved.