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1,5,6,7-Tetrahydro-2H-[1,4]diazepin-5,7-dione aus Malonimiden und 3-Dimethylamino-2,2-dimethyl-2H-azirin


Scholl, Bernhard; Bieri, Jost H; Heimgartner, Heinz (1978). 1,5,6,7-Tetrahydro-2H-[1,4]diazepin-5,7-dione aus Malonimiden und 3-Dimethylamino-2,2-dimethyl-2H-azirin. Helvetica Chimica Acta, 61(8):3050-3067.

Abstract

Reaction of the aminoazirine 1 with malonimides of type 7 in 2-propanol at room temperature leads to the 1,4-diazepine derivatives of type 9 (Scheme 3). The structure of 6,6-diethyl-3-dimethylamino-2,2-dimethyl-1,5,6,7-tetrahydro-2H-[1,4]diazepin-5,7-dione (9a) has been proved by single crystal X-ray analysis (Chapter 4). Reduction of the 7-membered heterocycle 9a with sodium borohydride yields the perhydro-[1,4]diazepin-5,7-dione 10, while 9a in ethanol at 60° undergoes a ring contraction to the 4H-imidazole derivative 11a (Scheme 4): Mechanisms of these two reactions are discussed in comparison with previously reported reactions (Chapter 5).

Abstract

Reaction of the aminoazirine 1 with malonimides of type 7 in 2-propanol at room temperature leads to the 1,4-diazepine derivatives of type 9 (Scheme 3). The structure of 6,6-diethyl-3-dimethylamino-2,2-dimethyl-1,5,6,7-tetrahydro-2H-[1,4]diazepin-5,7-dione (9a) has been proved by single crystal X-ray analysis (Chapter 4). Reduction of the 7-membered heterocycle 9a with sodium borohydride yields the perhydro-[1,4]diazepin-5,7-dione 10, while 9a in ethanol at 60° undergoes a ring contraction to the 4H-imidazole derivative 11a (Scheme 4): Mechanisms of these two reactions are discussed in comparison with previously reported reactions (Chapter 5).

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Other titles:1,5,6,7-Tetrahydro-2H-[1,4]diazepin-5,7-diones from Malonimides and 3-Dimethylamino-2,2-dimethyl-2H-azirine
Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis
Language:German
Date:1978
Deposited On:24 Aug 2014 08:29
Last Modified:18 Aug 2018 16:42
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0018-019X
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/hlca.19780610830
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSchweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung

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