Syntheses of 3,4-disubstituted pyrroles and furans via Lewis acid-promoted semipinacol rearrangement/alkyne-ketone metathesis reaction of (C)-2- N - Or O-((3-arylpropargyl)methyl)-tethered 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones

Ming Chang P. Yeh*, Ming Nan Lin, Ching Hsien Hsu, Chia Jung Liang

*此作品的通信作者

研究成果: 雜誌貢獻期刊論文同行評審

22 引文 斯高帕斯(Scopus)

摘要

The synthesis of 2,3-disubstituted pyrroles via TMSOTf-assisted cyclization reaction of 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones incorporating a (3-arylpropargyltosylamino)methyl tether at the C-2 position is described. The reaction starts with an acid-promoted semipinacol rearrangement to give a ring contraction cyclopentanone moiety bearing an arylpropargylaminoacetyl side chain. A subsequent alkyne-ketone metathesis affords the pyrrole derivatives in good yields. The 3,4-disubstituted furan analogues can also be available from 3,5,5-trimethyl-2,3-epoxycyclohexan-1-ones with a tethered arylpropargyl methyl ether at the C-2 position and BF3·OEt2 under an atmosphere of oxygen.

原文英語
頁(從 - 到)12381-12396
頁數16
期刊Journal of Organic Chemistry
78
發行號24
DOIs
出版狀態已發佈 - 2013 12月 20

ASJC Scopus subject areas

  • 有機化學

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