Abstract
The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1a) with 4,S-dihydro-7,8-dimethoxy-l,2-benzothiazepin-3-one 1,1-dioxide (4) in dioxane at room temperature gave the correspondingly substituted 4H-1,2,5- benzothiadiazecin-6-one 1,1-dioxide 5a in 64% yield (Scheme 2). The structure of this novel ten-membered ring-enlargement product was established by X-ray crystallography (Fig.). Under more vigorous conditions (refluxing dichloroethane), 5a was formed together with the isomeric 6a, both in low yield. The 3-(dimethylamino)-2H-azirines 1b and 1c reacted sluggishly to give the two isomeric ring-enlargement products of type 5 and 6 in yields of 24-29 % and 2-4 % , respectively (Table 1 ). Even less reactive is 2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine (1d), which reacted with 4 in MeCN only at 65°. Under these conditions, besides numerous decomposition products, only traces of 5d and 6d were formed. No ring enlargement was observed with the sterically crowded 1e, which bears an isopropyl group at C(2).
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: | English |
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Date: | 1996 |
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Deposited On: | 25 Nov 2013 08:19 |
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Last Modified: | 10 Jul 2025 01:36 |
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Publisher: | Wiley-Blackwell Publishing, Inc. |
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ISSN: | 0018-019X |
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Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel, Professor Hans E. Schmid-Stiftung |
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OA Status: | Closed |
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Publisher DOI: | https://doi.org/10.1002/hlca.19960790420 |
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Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Swiss National Science Foundation
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche AG, Basel
- Funder:
- Grant ID:
- Project Title: Professor Hans E. Schmid-Stiftung
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