Mihova, Tonya R; Linden, Anthony; Heimgartner, Heinz (1996). Synthesis of 1,2,5-Thiadiazepine Derivatives by Ring Enlargement of 1,2-Thiazetidin-3-one 1,1-Dioxides with 3-Amino-2H-azirines. Helvetica Chimica Acta, 79(8):2067-2074.
At 0° in MeCN, 2,2-disubstituted 3-amino-2H-azirines 1 and 4,4-disubstituted 1,2-thiazetidin-3-one 1,1-dioxides 7 react smoothly to give 1,2,5-thiadiazepin-6-one 1,1-dioxides of type 8 (Scheme 2). The reaction mechanism of this regiospecific ring enlargement to seven-membered heterocycles follows previously described pathways. The structures of 7a and 8h were established by X-ray crystallography (see Figs. I and 2).
At 0° in MeCN, 2,2-disubstituted 3-amino-2H-azirines 1 and 4,4-disubstituted 1,2-thiazetidin-3-one 1,1-dioxides 7 react smoothly to give 1,2,5-thiadiazepin-6-one 1,1-dioxides of type 8 (Scheme 2). The reaction mechanism of this regiospecific ring enlargement to seven-membered heterocycles follows previously described pathways. The structures of 7a and 8h were established by X-ray crystallography (see Figs. I and 2).
| Item Type: | Journal Article, refereed, original work |
|---|---|
| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
| Dewey Decimal Classification: | 540 Chemistry |
| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
| Language: | English |
| Date: | 1996 |
| Deposited On: | 25 Nov 2013 08:01 |
| Last Modified: | 04 Dec 2018 14:50 |
| Publisher: | Wiley-Blackwell |
| ISSN: | 0018-019X |
| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel |
| OA Status: | Closed |
| Publisher DOI: | https://doi.org/10.1002/hlca.19960790803 |
| Project Information: |
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Mihova, Tonya R