A one-pot, two step synthesis of 2,2-disubstituted 1-nitroalkenes

Yeong Jiunn Jang, Wen Wei Lin, Yuh Kuo Shih, Ju Tsung Liu, Ming Hsing Hwang, Ching Fa Yao*

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

14 引文 斯高帕斯(Scopus)

摘要

The reactions of ketones 1a-o, nitromethane 2, and a stoichiometric amount of piperidine 3a or ethylenediamine 3b in the presence of mercaptan 6a in THF or CH3CN solution give high yields of β-nitrosulfides 7a-o. The latter can be oxidized by 8a (m-CPBA or m-CPBA/AcOH) at 0°C, 8b (H2O2/AcOH), or 8c (H2O2) at room temperature, thus generating β-nitroalkylsulfoxides 9a-o, which then undergo elimination to produce medium to high yields of 2,2-disubstituted-1-nitroalkenes 5a-o, when refluxed in a solution of ClCH2CH2Cl (1,2-dichloroethane). After preparation from 1a-o, 2, 3, and 6a, 7a-o were oxidized with 8a, 8b, or 8c in a mixture of CH3CN and ClCH2CH2Cl to generate β-nitrosulfoxides 9a-o, which then underwent elimination under refluxing under one-pot conditions. Compounds 14 and 15g were also prepared using 13, 2, 3b, and 6, in a similar manner.

原文英語
頁(從 - 到)4979-4992
頁數14
期刊Tetrahedron
59
發行號27
DOIs
出版狀態已發佈 - 2003 6月 30

ASJC Scopus subject areas

  • 生物化學
  • 藥物發現
  • 有機化學

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