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- Title
1, 5, 6, 7-Tetrahydro-2H-[1,4]diazepin-5,7-dione aus Malonimiden und 3-Dimethylamino-2,2-dimethyl-2H-azirin.
- Authors
Scholl, Bernhard; Bieri, Jost H.; Heimgartner, Heinz
- Abstract
1, 5, 6, 7-Tetrahydro-2H-[1, 4]diazepin-5, 7-diones from Malonimides and 3-Dimethylamino-2, 2-dimethyl-2H-azirine 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 4 H-imidazole derivative 11a ( Scheme 4): Mechanisms of these two reactions are discussed in comparison with previously reported reactions (Chapter 5).
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 8, p3050
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610830