Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen
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 chemica...
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| Main Authors: | , |
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| Format: | Article |
| Language: | deu |
| Published: |
Swiss Chemical Society
1978-12-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9427 |
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| Summary: | 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 ratio of the two isomers depends on the solvent.
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| ISSN: | 0009-4293 2673-2424 |