Synthesis of aminoquinolones from triazoles via carboxamidoketenimine and amidinoketene intermediates

Abstract

1-Aryl-1H-1,2,3-triazole-4-carboxamides 7d–f have been synthesized and converted to 2-dimethylamino-4-quinolones 12d–f by flash vacuum thermolysis (FVT). The reaction takes place via carboxamidoketenimine 9 and amidinoketene intermediates 10. The former are observed by FTIR spectroscopy at 77 K or in Ar matrices at 12 K.

References

1. D. Clarke, R. W. Mares and H. McNab, J. Chem. Soc., Chem. Commun., 1993, 1020; J. Chem. Soc., Perkin Trans. 1, 1997, 1799.
2. B. E. Fulloon and C. Wentrup, J. Org. Chem., 1996, 61, 1363.
3. B. E. Fulloon, H. A. A. El-Nabi, G. Kollenz and C. Wentrup, Tetrahedron Lett., 1995, 36, 6547.
4. (a) C. O. Kappe, G. Kollenz, R. Leung-Toung and C. Wentrup, J. Chem. Soc., Chem. Commun., 1992, 487; (b) M. W. Wong and C. Wentrup, J. Org. Chem., 1994, 59, 5279; (c) D. W. J. Moloney, M. W. Wong, R. Flammang and C. Wentrup, J. Org. Chem., 1997, 62, 4240; (d) V. V. R. Rao, B. E. Fulloon, P. V. Bernhardt, R. Koch and C. Wentrup, J. Org. Chem., 1998, 63 in the press; (e) C. Wentrup, B. E. Fulloon, D. W. J. Moloney, H. Bibas and M. W. Wong, Pure Appl. Chem., 1996, 68, 891; (f) J. Finnerty, J. Andraos, Y. Yamamoto, M. W. Wong and C. Wentrup, J. Am. Chem. Soc., 1998, 120, 1701; (g) M. W. Wong and C. Wentrup, unpublished calculations.
5. D. Niccolai, L. Tarsi and R. J. Thomas, Chem. Commun., 1997, 2333; K. Grohe, Chem. Brit., 1992, 34; Y. Asahina, T. Ishizaki and S. Suzue, in Progress in Drug Research, ed. S. Mitsuhashi, Birkhauser, Basel, 1992, vol. 38, pp. 57–106.
6. S.-C. Kuo, H.-Z. Lee, J.-P. Juang, Y.-T. Lin, T.-S. Wu, J.-J. Chang, D. Lednicer, K. D. Paull, C. M. Lin, E. Hamel and K.-H. Lee, J. Med. Chem., 1993, 36, 1146.
7. G. Himbert, in Houben-Weyl: Methoden der Organischen Chemie; Thieme Verlag, Stuttgart, 1993, vol. E 15/3, p. 3426, and references therein; M. E. Kuehne and P. J. Sheehan, J. Org. Chem., 1968, 33, 4406; K. T. Potts, R. Ehlinger and W. M. Nichols, J. Org. Chem., 1975, 40, 2596.
8. (a) N-Phenylketenimine absorbs in N₂ matrix at 2050, 2030 cm^–1.^8b In Ar matrix it absorbs at 2048, 2032 cm^–1,^8c and in CCl₄ solution at room temperature at 2040, 2020 cm^–1(both absorptions are very strong);^8d; (b) E. Orton, S. T. Collins and G. C. Pimentel, J. Phys. Chem., 1986, 90, 6139; (c) B. Freiermuth and C. Wentrup, previously unpublished measurements; (d) H.-W. Winter and C. Wentrup, Angew. Chem., Int. Ed. Engl., 1980, 19, 720.
9. (a) N-Methylmethanimine: H. Bibas, R. Koch and C. Wentrup, J. Org. Chem., 1998, 63, 2619; (b) N-Phenyliminopropadienone: T. Mosandl, S. Stadtmüller, M. W. Wong and C. Wentrup, J. Phys. Chem., 1994, 98, 1080; (c) Phenyl isocyanate: C. O. Kappe, G. Kollenz and C. Wentrup, Acta Chem. Scand., 1993, 47, 940.
10. H. Briehl, A. Lukosch and C. Wentrup, J. Org. Chem., 1984, 49, 2772.
11. D. J. W. Moloney, PhD Thesis, The University of Queensland, 1997; A. Bouvy, Z. Janousek, H. G. Viehe and J. M. Arietta, Bull. Soc. Chim. Belg., 1985, 94, 869.
12. C. Wentrup, Reactive Molecules, Wiley, New York, 1984, p. 225.
13. C. O. Kappe, M. W. Wong and C. Wentrup, J. Org. Chem., 1995, 60, 1686–1895.
14. C. Wentrup, R. Blanch, H. Briehl and G. Gross, J. Am. Chem. Soc., 1988, 110, 1874.
15. S. T. Abu-Orabi, M. A. Atfah, I. Jibril, F. M. Mari'i and A. A. Ali, J. Heterocycl. Chem., 1989, 26, 1461; R. Huisgen, R. Knorr, L. Möbius and G. Szeimies, Chem. Ber., 1965, 98, 4014.
16. I. Hermecz, G. Kereszturi and L. Vasvari-Debreczy, Adv. Heterocycl. Chem., 1992, 54, 252 and references therein.