Formation of pyridin-4(1H)-one versus 1H-azepin-4(7H)-one by treatment of 4-tert-butyldimethylsilyloxy-2-amino-1-aza-bicyclo[4.1.0]hept-3-enes with tetrabutylammonium fluoride |
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| Authors: | M José Alves A Gil Fortes Vera CM Duarte |
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| Institution: | a Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
b Faculdade de Ciências da Saúde, Universidade Fernando Pessoa, R. Carlos da Maia 298, 4200-150 Porto, Portugal |
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| Abstract: | Cycloadducts 3 and 4 were treated with tetrabutylammonium fluoride and rapidly suffer cleavage on the three-membered ring to form either pyridin-4(1H)-one or 1H-azepin-4(7H)-one. When R1 is an oxycarbonyl or a 2-pyridyl group and R2 is a negative charge-stabilizing group (cases 3a,b and 4f) the C-C bond cleaves forming products 5. However, when R2=H (case 3c) the ring expands to seven members. When R1 is an acyl group the pyridin-4(1H)-one formation includes an unexpected shift of the carbonyl group. |
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| Keywords: | Azepinones Pyridinones Aziridines Tetrabutylammonium fluoride |
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