N,1-dialkyl-7-(alkylamino)-4-(alkylimino)-1,4-dihydroquinoline-3- carboxamides and their 4-oxo derivatives: Synthesis and properties

South African Journal of Chemistry

Volumn 54, Issue , 2001, Pages 102-117

  Van Es, Theodorus ^a   Staskun, Benjamin ^b  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Mechanism; Quinolin 4 imines; Quinolin 4 ones

Indexed keywords

AMIDE; AMINE; CARBOXYLIC ACID DERIVATIVE; CHLORIDE; ESTER DERIVATIVE; HYDROGEN;

ARTICLE; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS;

EID: 4243053162     PISSN: 03794350     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (10)

1. T. van Es and B. Staskun, J. Chem. Soc., Perkin Trans.1, 1998, 3137.
2. Structural representation 2 (Scheme 1) for the complex is currently preferred to that shown in Reference 1.
3. 4-Imino amides 4h, 4i and 4j (Table 1) which appear in Reference 1 are here represented for spectral structure verifications (Experimental).
4. More vigorous reaction conditions are generally utilised to effect nucleophilic substitution of the 7-F in 1-alkyl-4(1H)-quinolone derivatives, as exemplified in the contributions by (a) K. Grohe and H. Heitzer, Liebigs Ann. Chem., 1987, 29; and
5. (b) K. Grohe, J. Prakt. Chem., 1993, 335, 397.
6. R.U. Schock, J. Am. Chem. Soc., 1957, 79, 1670.
7. T. van Es and B. Staskun, unpublished results.
8. Other methods for preparing related 4-oxo amides 5 include (i) converting the appropriate quinolone-3-carboxylic acid into its acylimidazole derivative, followed by treatment with the requisite amine, and (ii) amidating a quinolone-3-carboxylic ester in a stainless steel bomb containing the amine. M.P. Wentland, R.B. Perni, P.H. Dorff, R.P. Brundage, M.J. Castaldi, T.R. Bailey, P.M. Carabateas, E.R. Bacon, D.C. Young, M.G. Woods, D. Rosi, M.L. Drozd, R.K. Kullnig and F.J. Dutko, J. Med. Chem., 1993, 36, 1580.
9. H. Agui, T. Mitani, N. Nakashita and T. Nakagome, J. Heterocycl. Chem., 1971, 8, 357.
10. B. Staskun and T. van Es, S. Afr. J. Chem., 1998, 51, 92.