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Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen


Chaloupka, Stanislav; Heimgartner, Heinz (1978). Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen. CHIMIA International Journal for Chemistry, 32(12):468-470.

Abstract

Reaction of the 3-dimethylamino-2H-azirines 1a and 1b with diphenylcyclopropenone (2a) in ether or acetonitrile leads to the 2-dimethylamino-5,6-diphenyl-4(3H)-pyridones 3a and 3b in 70 and 80% yield, respectively. The structure of these 1:1-adducts has been established by spectral data and chemical reactions. Hydrolysis of 3a yields the pyridinedione derivative 5 whereas reduction of 3a with sodium borohydride gives the dihydropyridone 6. The reaction of aminoazirine 1c, monosubstituted at C(2), with 2a gives the 4(1H)-pyridone 4. With alkyl phenylcyclopropenones (2b and 2c) aminoazirine 1a reacts to give a mixture of two isomeric 4(3H)-pyridones. The ration of the two isomers depends on the solvent.

Abstract

Reaction of the 3-dimethylamino-2H-azirines 1a and 1b with diphenylcyclopropenone (2a) in ether or acetonitrile leads to the 2-dimethylamino-5,6-diphenyl-4(3H)-pyridones 3a and 3b in 70 and 80% yield, respectively. The structure of these 1:1-adducts has been established by spectral data and chemical reactions. Hydrolysis of 3a yields the pyridinedione derivative 5 whereas reduction of 3a with sodium borohydride gives the dihydropyridone 6. The reaction of aminoazirine 1c, monosubstituted at C(2), with 2a gives the 4(1H)-pyridone 4. With alkyl phenylcyclopropenones (2b and 2c) aminoazirine 1a reacts to give a mixture of two isomeric 4(3H)-pyridones. The ration of the two isomers depends on the solvent.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:December 1978
Deposited On:19 Aug 2014 14:11
Last Modified:05 Apr 2016 18:01
Publisher:Swiss Chemical Society
ISSN:0009-4293
Funders:Schweizerischer Nationalfonds zur Förderung der wissenschaftlichen Forschung

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