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Carbon‐nitrogen bond formation in cyclisation by deoxygenation, thermolysis or photolysis of phenylimidazo[1,2‐ a ][1,8]naphthyridines

1992; Wiley; Volume: 29; Issue: 2 Linguagem: Inglês

10.1002/jhet.5570290202

1943-5193

Alain Gueiffier, Yves Blache, H. VIOLS, J. P. CHAPAT, Olivier Chavignon, Jean‐Claude Teulade, G. DAUPHIN, J.C. Debouzy, J. L. Chabard,

Synthesis and Reactions of Organic Compounds

Abstract Triethyl phosphite deoxygenation of 2‐(2‐nitrophenyl)imidazo[1,2‐ 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)imidazo[1,2‐ a ][1,8]‐naphthyridine (12) led to the corresponding amine structure (15). Thermolysis and photolysis of 6,8‐dimethyl‐2‐(2‐azidophenyl)imidazo[1,2‐ a ][1,8]naphthyridine (17) are also reported.