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 |
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頁(從 - 到) | 12381-12396 |
頁數 | 16 |
期刊 | Journal of Organic Chemistry |
卷 | 78 |
發行號 | 24 |
DOIs | |
出版狀態 | 已發佈 - 2013 12月 20 |
對外發佈 | 是 |
ASJC Scopus subject areas
- 有機化學
指紋
深入研究「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」主題。共同形成了獨特的指紋。資料集
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CCDC 946900: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, M. (Creator), Hsu, C. (Creator) & Liang, C. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc10sb59, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10sb59&sid=DataCite
資料集: Dataset
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CCDC 946905: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, M. (Creator), Hsu, C. (Creator) & Liang, C. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc10sbbg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10sbbg&sid=DataCite
資料集: Dataset
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CCDC 946897: Experimental Crystal Structure Determination
Yeh, M. P. (Creator), Lin, M. (Creator), Hsu, C. (Creator) & Liang, C. (Creator), Unknown Publisher, 2014
DOI: 10.5517/cc10sb26, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc10sb26&sid=DataCite
資料集: Dataset