Abstract
Reaction of the aminoazirine 1 and malonic acid monoamides 5 in CH3CN yielded triamides of type 6 (Scheme 2), which were transformed to the corresponding phenylthioates 9 by treatment of a solution of 6 and thiophenol in CH3CN with HCI (Scheme 4). Cyclization of 9 to give the 1,4-diazepin-2,5,7-trione of type 10 was achieved with NaH in toluene at about 90°. It has been shown that 2-oxazolin-5-ones are intermediates in the selective cleavage of the terminal amide function of 6 (Scheme 3 ) .
| Other titles: | Synthesis of 3,3-Dimethylperhydro-1,4-diazepin-2,5,7-triones from 3-Dimethylamino-2,2-dimethyl-2H-azirine and Malonic Acid Monoamides |
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| Item Type: | Journal Article, refereed, original work |
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| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
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| Dewey Decimal Classification: | 540 Chemistry |
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| 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 |
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| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
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| Language: | German |
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| Date: | 1985 |
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| Deposited On: | 16 Jun 2014 11:15 |
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| Last Modified: | 11 Mar 2025 02:38 |
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| Publisher: | Wiley-Blackwell |
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| ISSN: | 0018-019X |
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| Funders: | Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung, F. Hoffmann-La Roche & Co. AG, Basel, Dr. Emil-Bindschedler-Fonds |
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| OA Status: | Closed |
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| Publisher DOI: | https://doi.org/10.1002/hlca.19850680220 |
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| Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche & Co. AG, Basel
- Funder:
- Grant ID:
- Project Title: Dr. Emil-Bindschedler-Fonds
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Obrecht, Daniel