𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Ringerweiterung von 1,2-Thiazol-3(2H)-on-1,1-dioxiden und 3-Amino-2H-azirinen zu 4H-1,2,5-Thiadiazocin-6-on-1,1-dioxiden

✍ Scribed by Annette Rahm; Anthony Linden; Beverly R. Vincent; Heinz Heimgartner; Manfred Mühlstädt; Bärbel Schulze

Publisher
John Wiley and Sons
Year
1991
Tongue
German
Weight
531 KB
Volume
74
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Ring Enlargement of 1,2-Thiazol-3(2H)-one-l,l-dioxides and 3-Amino-2H-azirines to 4H-1,2,S-Thiadiazocin-6-one-l, 1-dioxides

Reaction of 3-amino-2H-azirines 2 with the 1,l-dioxides 4 and 7 of 1,2-thiazol-3(2H)-ones and 1,2-thiazolidin-3-ones, respectively, in i-PrOH at room temperature leads to 4H-1,2,5-thiadiazocin-6(SH)-one-1,l-dioxides S (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 (Chupt. 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 (I-'5N)-labelled aminoazirine 2a*.

📜 SIMILAR VOLUMES

Zur Oxidation von 1,2-Thiazolen: Ein ein
Zur Oxidation von 1,2-Thiazolen: Ein einfacher Zugang zu 1,2-Thiazol-3(2H)-on-1,1-dioxiden
✍ Bärbel Schulze; Gisela Kirsten; Sabine Kirrbach; Annette Rahm; Heinz Heimgartner 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 German ⚖ 734 KB

Oxidation of 1,2‐Thiazoles; A Convenient Approach to 1,2‐Thiazol‐3(2__H__)‐one 1,1‐Dioxides The 1,2‐thiazoles obtained from 3‐chloroalk‐2‐enals and ammonium thiocyanate (7 → 9, __Scheme 1__) are easily transformed to 1,2‐thiazol‐3(2__H__)‐one 1,1‐dioxidcs 10 on treatment with H~2~O~2~ in AcOH at 80

Ringerweiterung von sechs- zu neungliedr
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
✍ Marlise Schläpfer-Dähler; Heinz Heimgartner 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 German ⚖ 527 KB

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‐benzothiadi

Synthesen von 2H-1,2-Benzothiazin-1,1-di
Synthesen von 2H-1,2-Benzothiazin-1,1-dioxiden, I. Neue 4-Hydroxy-2H-1,2-benzothiazin- und 4-Hydroxy-2H-naphtho[2,1-e]-1,2-thiazin-3-carboxamid-1,1-dioxide
✍ Steiner, Gerd 📂 Article 📅 1978 🏛 Wiley (John Wiley & Sons) ⚖ 421 KB 👁 1 views

## Abstract Neue 4‐Hydroxy‐2__H__‐1,2‐benzothiazin‐3‐carboxamid‐1,1‐dioxide **1** stellte man durch Aminolyse des entsprechenden Carbonsäureesters **2** her. Die analogen Naphtho[2,1‐e]‐1,2‐thiazin‐1,1‐dioxide **3** wurden in einer 5‐Stufen‐synthese aufgebaut.