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Ringerweiterung von sechs- zu neungliedrigen Heterocyclen: Umsetzung von 3-(Dimethylamino)-2,2-dimethyl-2H-azirin mit 3,4-Dihydro-2H-1,2,4-benzothiadiazin-3-on-1,1-dioxiden

✍ Scribed by Marlise Schläpfer-Dähler; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1993
Tongue
German
Weight
527 KB
Volume
76
Category
Article
ISSN
0018-019X

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✦ Synopsis

Ring Enlargement of Six‐ to Nine‐Membered Heterocycles: Reaction of 3‐(Dimethylamino)‐2,2‐dimethyl‐2__H__‐azirine with 3,4‐Dihydro‐2__H__‐1,2,4‐benzothiadiazin‐3‐one 1,1‐Dioxides

Reaction of 3‐(dimethylamino)‐2,2‐dimethyl‐2__H__‐azirine (1) and N‐substituted 3,4‐dihydro‐2__H__‐1,2,4‐benzothiadiazin‐3‐one 1,1‐dioxides (4) in CHCl~3~ yields 3‐(dimethylamino)‐4,5,6,7‐tetrahydro‐1,2,5,7‐benzothiatriazonin‐6‐one 1,1‐dioxides 5, a novel nine‐membered heterocyclic system, by ring enlargement (Schemes 2 and 4). In refluxing MeOH, the heterocycle 5a rearranges to give the N‐[1‐methyl‐1‐(1,1‐dioxo‐4__H__‐1,2,4‐benzothiadiazin‐3‐yl)ethyl]‐N′, N′‐dimethylurea 10. The three isomeric 2‐(methylamino)benzenesufonamides 8,9, and 11 (Scheme 3) are obtained by naBH~4~ reduction of 5a and 10, respectively. Mechanisms for the thermal isomerization 5a → 10 and the NaBH~4~ reduction of 5a are proposed in Schemes 5 and 6.

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