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Zur Oxidation von 1,2-Thiazolen: Ein einfacher Zugang zu 1,2-Thiazol-3(2H)-on-1,1-dioxiden


Schulze, Bärbel; Kirsten, Gisela; Kirrbach, Sabine; Rahm, Annette; Heimgartner, Heinz (1991). Zur Oxidation von 1,2-Thiazolen: Ein einfacher Zugang zu 1,2-Thiazol-3(2H)-on-1,1-dioxiden. Helvetica Chimica Acta, 74(5):1059-1070.

Abstract

The 1,2-thiazoles obtained from 3-chloroalk-2-enals and ammonium thiocyanate (7 to 9, Scheme 1) are easily transformed to 1,2-thiazol-3(2H)-one 1,1-dioxides 10 on treatment with H202 in AcOH at 80°. Hydrogenation of 10 in AcOH yields the corresponding saturated 1,2-thiazolidin-3-one 1,1-dioxides 16 (Scheme 3). Cycloalka[c]-1,2-thiazoles 18 are prepared from 2-[(thiocyanato)methyliden]cycloalkan-l-ones and ammonia (Scheme 4). Surprisingly, oxidation of 18a with H202 in AcOH yields the tricyclic oxaziridine 19.

Abstract

The 1,2-thiazoles obtained from 3-chloroalk-2-enals and ammonium thiocyanate (7 to 9, Scheme 1) are easily transformed to 1,2-thiazol-3(2H)-one 1,1-dioxides 10 on treatment with H202 in AcOH at 80°. Hydrogenation of 10 in AcOH yields the corresponding saturated 1,2-thiazolidin-3-one 1,1-dioxides 16 (Scheme 3). Cycloalka[c]-1,2-thiazoles 18 are prepared from 2-[(thiocyanato)methyliden]cycloalkan-l-ones and ammonia (Scheme 4). Surprisingly, oxidation of 18a with H202 in AcOH yields the tricyclic oxaziridine 19.

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Additional indexing

Other titles:Oxidationof 1,2-Thiazoles: A Convenient Approachto 1,2-Thiazol-3(2H)-one 1,1-Dioxides
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1991
Deposited On:13 Mar 2014 08:19
Last Modified:05 Apr 2016 17:26
Publisher:Wiley-Blackwell
ISSN:0018-019X
Publisher DOI:https://doi.org/10.1002/hlca.19910740515

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