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- Title
Ringerweiterung von 1,2-Thiazol-3(2 H)-on-1,1-dioxiden und 3-Amino-2 H-azirinen zu 4 H-1,2,5-Thiadiazocin-6-on-1,1-dioxiden.
- Authors
Rahm, Annette; Linden, Anthony; Vincent, Beverly R.; Heimgartner, Heinz; Mühlstädt, Manfred; Schulze, Bärbel
- Abstract
Ring Enlargement of 1,2-Thiazol-3(2 H)-one-1,1-dioxides and 3-Amino-2 H-azirines to 4 H-1,2,5-Thiadiazocin-6-one-1,1-dioxides Reaction of 3-amino-2 H-azirines 2 with the 1,1-dioxides 4 and 7 of 1,2-thiazol-3(2 H)-ones and 1,2-thiazoli-din-3-ones, respectively, in i-PrOH at room temperature leads to 4 H-1,2,5-thiadiazocin-6(5 H)-one-1,1-dioxides 5 ( Scheme 2, Table) and the corresponding 7,8-dihydro derivatives 8 ( Scheme 4), respectively. The structure of some of the new 8-membered heterocycles as well as the structure of the minor by-product 6 ( Scheme 3) have been established by X-ray crystallography ( Chapt. 4). The proposed reaction mechanism for the ring expansion to 5 and 8 ( Scheme 2) is in accordance with previously published results of reactions of 2 and NH-acidic heterocycles and is further supported by the results of the reaction of 4a and the (1-15N)-labelled aminoazirine 2a*.
- Publication
Helvetica Chimica Acta, 1991, Vol 74, Issue 5, p1002
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19910740511