Carbon-nitrogen bond formation in cyclisation by deoxygenation,thermolysis or photolysis of phenylimidazo[1,2-a][1,8]naphthyridines |
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Authors: | A Gueiffier Y Blache H Viols J P Chapat O Chavignon J C Teulade G Dauphin J C Debouzy J L Chabard |
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Abstract: | Triethyl phosphite deoxygenation of 2-(2-nitrophenyl)imidazo1,2-a]1,8]naphthyridine (3) led to the C-insertion to give the indoloimidazonaphthyridine 5. Our attempt to promote the N-insertion by blocking the C-3 position failed. Triethyl phosphite deoxygenation of 1-nitroso-2-(4-fluorophenyl)imidazo1,2-a]1,8]-naphthyridine (12) led to the corresponding amine structure (15). Thermolysis and photolysis of 6,8-dimethyl-2-(2-azidophenyl)imidazo1,2-a]1,8]naphthyridine (17) are also reported. |
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