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Synthesis of 1,2,5-Thiadiazepine Derivatives by Ring Enlargement of 1,2-Thiazetidin-3-one 1,1-Dioxides with 3-Amino-2H-azirines

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.

Abstract

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).

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic 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:09 Jun 2025 01:41
Publisher:Wiley-Blackwell Publishing, Inc.
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:
  • Funder: SNSF
  • Grant ID:
  • Project Title: Swiss National Science Foundation
  • Funder:
  • Grant ID:
  • Project Title: F. Hoffmann-La Roche AG, Basel

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