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Heimgartner, H; Linden, Anthony; Mekhael, M K G (2011). Reactions with 4-Hydroxy-2-methylbutananilides – unexpected formation of a cyclopropanecarboxamide. Helvetica Chimica Acta, 94(1):28-37.
The successive treatment of the N,N-disubstituted 4-hydroxy-2-methylbutanamide 2a with LDA and diphenyl phosphorochloridate (DPPCl) led to the 1-methylcyclopropanecarboxamide 10 in good yield. This base-catalyzed cyclization offers a new approach to cyclopropanecarboxamides. Under similar conditions, the N-monosubstituted 4-hydroxy-2-methylbutanamide 2b gave the 3-methylpyrrolidin-2-one 11. The structure of the cyclopropanecarboxamide 10 was established by X-ray crystallography.
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry Life Sciences > Drug Discovery Physical Sciences > Physical and Theoretical Chemistry Physical Sciences > Organic Chemistry Physical Sciences > Inorganic Chemistry |
| Language: | English |
| Date: | January 2011 |
| Deposited On: | 08 Feb 2011 16:38 |
| Last Modified: | 05 Mar 2025 02:39 |
| Publisher: | Verlag Helvetica Chimica Acta |
| ISSN: | 0018-019X |
| Funders: | Schweizerischer Nationalfonds (SNF), F. Hoffmann-La Roche AG, Basel |
| OA Status: | Green |
| Publisher DOI: | https://doi.org/10.1002/hlca.201000370 |
| Project Information: |
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Heimgartner, H