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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.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Yeh, Ming-Chang P. Lin, Ming-Nan Hsu, Ching-Hsien Liang, Chia-Jung |
| Copyright Year | 2013 |
| Abstract | 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. |
| File Format | PDF HTM / HTML |
| DOI | 10.1021/jo402025z |
| Alternate Webpage(s) | http://www.chem.ntnu.edu.tw/files/writing/1844_3f6cfa59.pdf |
| PubMed reference number | 24294833 |
| Alternate Webpage(s) | https://doi.org/10.1021/jo402025z |
| Journal | Medline |
| Volume Number | 78 |
| Issue Number | 24 |
| Journal | The Journal of organic chemistry |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
