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α-Oxolactam enamines as new synthons in the Nenitzescu reaction

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Abstract

α-Oxolactam enamines, namely, 3-piperidino-5,6-dihydropyridin-2(1H)-one (1a) and 3-piperidino-1,5,6,7-tetrahydroazepin-2-one (1b), were introduced for the first time into the Nenitzescu reaction. The processes yield cyclic adducts 3a—e, 6. On heating in acetic acid, they are transformed into benzofuropyridone 7 and benzofuroazepinones 10a,d, and 12 and, unexpectedly, into chromenopyrrole 8 and chromenopyridines 9a—d and 11.

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Lyubchanskaya, V.M., Alekseeva, L.M., Savina, S.A. et al. α-Oxolactam enamines as new synthons in the Nenitzescu reaction. Russian Chemical Bulletin 51, 1886–1893 (2002). https://doi.org/10.1023/A:1021308719984

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