1-alkyl-1,4-dihydro-4-imino-3-quinolinecarboxylates. Part 1. General synthesis

South African Journal of Chemistry

Volumn 51, Issue 2, 1998, Pages 92-99

  Staskun, Benjamin ^a   Van Es, Theodorus ^b  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b NONE

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[No Author keywords available]

Indexed keywords

EID: 0032342679     PISSN: 03794350     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. K. Grohe and H. Heitzer, Liebigs Ann. Chem., 1987, 29.
2. L.A. Mitscher, P.V. Devasthale and R.M. Zavod, The 4-Quinolones: Antibacterial Agents in Vitro, ed. G.C. Crumplin, Springer-Verlag, London, 1990, chap. 9.
3. D. Bouzard, Recent Progress in the Chemical Synthesis of Antibiotics, G. Lukacs and M. Ohno, eds, Springer-Verlag, Berlin, 1990, chap. 7.
4. R. Albrecht, Prog. Drug Res., 1977, 21, 9.
5. K. Grohe, J. Prakt. Chemie, 1993, 335, 397.
6. (a) Structurally related 7-arylimino-quinoline derivatives of type A, obtained from condensation of a ketone with a substituted guanidine, have been reported. J. Moszew, B. Adamczyk, M. Bala and W. Zankowska-Jasinka, Zesz. Nauk. Uniw. Jagiellon., Pr. Chem. 1966, 17 (Chem. Abstr., 1968, 69, 86850m) and references therein. (equation presented)
7. (a) Structurally related 7-arylimino-quinoline derivatives of type A, obtained from condensation of a ketone with a substituted guanidine, have been reported. J. Moszew, B. Adamczyk, M. Bala and W. Zankowska-Jasinka, Zesz. Nauk. Uniw. Jagiellon., Pr. Chem. 1966, 17 (Chem. Abstr., 1968, 69, 86850m) and references therein. (equation presented)
8. (b) 4-imino-(B)-and 4-ethylimino(C)-analogues of 2 have been obtained by cyclization of derivatives of 3-(N-alkylanilino)-acrylic acid with polyphosphoric ester. For example: K.. Okumura, T. Adachi, M. Tomie, K. Kondo and I. Inoue, J. Chem. Soc., Perkin Trans., 1972, 1, 173. (equation presented)
9. Numerous related 1-alkyl-4-(alkylimino and arylimino)-quinolines of type D have been reported: e.g. (i) Beilstein, vol. 21 (EIII/IV), 3764-3769;
10. Chem. Abstr., 1994, 122, 81145p. Their synthesis generally utilizes a preformed quinoline derivative as substrate. For example (loc. cit. (i)): (equation presented)
11. Chem. Abstr., 1994, 122, 81145p. Their synthesis generally utilizes a preformed quinoline derivative as substrate. For example (loc. cit. (i)): (equation presented)
12. B. Staskun and H. Stephen, J. Chem. Soc., 1956, 4696.
13. P.C. Anderson and B. Staskun, J. Org. Chem., 1965, 30, 3033.
14. 1 3-amino-2-butenoates 3a, thereby militating against the synthesis of 1-unsubstituted 4(1H)-quinolones by the cycloaracylation procedure.
15. T. van Es and B. Staskun. Unpublished work.
16. J. March, Advanced Organic Chemistry, 3rd edn. John Wiley, 1985, 587.
17. The cyclization of 7b to 13 is reminiscent of the acid-catalysed ring-closure of a 4-anilino-3-quinolinecarboxylic acid to a related dibenzo[b,h][1,6]naphthyridine derivative (W.O. Kermack and N.E. Storey, J. Chem. Soc., 1951, 1389).
18. P.E. Marecki and R.E. Bambury, J. Pharm. Science, 1984, 73, 1141.
19. D. Ilavsky!, Chemistry of Heterocyclic Compounds, eds J. Kovac and P. Zalupsky, Elsevier, 1988, p. 46.
20. The preparation and properties of these two classes of compounds will be discussed in a subsequent paper.
21. S. Glickman and A. Cope, J. Amer. Chem. Soc., 1945, 67, 1017.
22. F. Reverdin, Ber., 1909, 42, 1524.
23. 7