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Eine neue Aminoazirin-Reaktion. Bildung von 3,6-Dihydropyrazin-2(1H)-onen (1989)

Hugener, Martin ; Heimgartner, Heinz

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 72 (1989), S. 172-179

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A New Aminoazirine Reaction. Formation of 3,6-Dihydropyrazin-2(1H)-onesThe reaction of 3-(dimethylamino)-2H-azirines 1 and 2-(trifluoromethyl)-1,3-oxazol-5(2H)-ones 5 in MeCN or THF at 50-80° leads to 5-(dimethylamino)-3,6-dihydropyrazin-2(1H)-ones 6 (Scheme 3). Reaction mechanisms for the formation of 6 are discussed: either the oxazolones 5 react as CH-acidic heterocycles with 1 (Scheme 4), or the azirines 1 undergo a nucleophilic attack onto the carbonyl group of 5 (Scheme 6). The reaction via intermediate formation of N-(trifluoroacetyl)dipeptide amide 8 (Scheme 5) is excluded.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19890720123

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