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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| Format: | Article |
| Language: | deu |
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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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| _version_ | 1850170692874534912 |
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| author | Stanislav Chaloupka Heinz Heimgartner |
| author_facet | Stanislav Chaloupka Heinz Heimgartner |
| author_sort | Stanislav Chaloupka |
| collection | DOAJ |
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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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| format | Article |
| id | doaj-art-0679e610bbeb454fb746ecc0ee04febc |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1978-12-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-0679e610bbeb454fb746ecc0ee04febc2025-08-20T02:20:26ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241978-12-01321210.2533/chimia.1978.468Pyridonderivate aus 3-Amino-2H-azirinen und CyclopropenonenStanislav Chaloupka0Heinz Heimgartner1Organisch-chemisches Institut der Universität ZurichOrganisch-chemisches Institut der Universität Zurich 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. https://www.chimia.ch/chimia/article/view/9427 |
| spellingShingle | Stanislav Chaloupka Heinz Heimgartner Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen CHIMIA |
| title | Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen |
| title_full | Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen |
| title_fullStr | Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen |
| title_full_unstemmed | Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen |
| title_short | Pyridonderivate aus 3-Amino-2H-azirinen und Cyclopropenonen |
| title_sort | pyridonderivate aus 3 amino 2h azirinen und cyclopropenonen |
| url | https://www.chimia.ch/chimia/article/view/9427 |
| work_keys_str_mv | AT stanislavchaloupka pyridonderivateaus3amino2hazirinenundcyclopropenonen AT heinzheimgartner pyridonderivateaus3amino2hazirinenundcyclopropenonen |