Preparation and Some Reactions with 3-(Quinolin-3-yl)-3-Oxopropanoic Acid
DOI:
https://doi.org/10.29356/jmcs.v55i4.804Keywords:
Quinolin-2(1H)-one, β-Keto-carboxylic acid, Pyrano[3, 2- c]quinoline, Knoevenagel condensation, heterocyclization reactions.Abstract
Preparation of quinolinyl-3-oxopropanoic acid 2 was accomplished by hydrolysis of pyranoquinolinedione 1 in aqueous alkaline medium. The chemical behavior of this β-keto acid 2 towards nitrosation, coupling with a diazonium salt, esterification, condensation with 2,2-dimethoxyethanamine, hydrazinolysis, Knoevenagel condensation with isatine, salisyaldehyde, 3-formylquinolones, and 3- formylchromone, was investigated. Also many of the products of these reactions were found obtainable using either pyranoquinolinedione 1 or β-keto acid 2, under the same conditions.
Downloads
References
Abass, M.; Mostafa, B. B. Bioorg. Med. Chem. 2005, 13, 6133- 6144.
El-Shennawy, A. M.; Mohamed A. H.; Abass M. Medscape J. Med. 2007, 9, 15-33.
Detsi, A.; Bouloumbasi, D.; Prousis, K. C.; Koufaki, M.; Athanasellis, G.; Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. Med. Chem. 2007, 50, 2450-2458.
Rivkin, A.; Kim, Y. R.; Goulet, M. T.; Bays, N.; Hill, A. D.; Kariv, I.; Krauss, S.; Ginanni, N.; Strack, P. R.; Kohl, N. E.; Chung, C. C.; Varnerin, J. P.; 5. Goudreau, P. N.; Chang, A.; Tota, M. R.; Munoz, B. Bioorg. Med. Chem. Lett. 2006, 16, 4620-4623.
Tani, M.; Harimaya, K.; Gyobu, Y.; Sasaki, T.; Takennouchi, O.; Kawamura, T.; Kamimura, T.; Harada, T. J. Antibiot. 2004, 57, 89-96.
Snider, B. B.; Wu X. Heterocycles 2006, 70, 279-294.
Ahvale, A. B.; Prokopcová, H.; Šef?ovi?ová, J.; Steinschifter, W.; Täubl, A. E.; Uray, G.; Stadlbauer, W. Eur. J. Org. Chem. 2008, 563-571. 232 J. Mex. Chem. Soc. 2011, 55(4) Mohamed Abass et al.
Ukrainets, I. V.; Tkach, A. A.; Yang, L. Y. Chem. Heterocycl. Compds. 2008, 44, 1347 1354.
Mohamed, E. A.; Ismail, M. M.; Gabr, Y.; Abass, M.; Farrag, H. A. Indian J. Chem. 1995, 34B, 21-26.
Mohamed, E. A.; Ismail, M. M.; Gabr, Y.; Abass, M. J. Serb. Chem. Soc. 1993, 58, 737-743.
Stadlbauer, W.; Badawey, E.; Hojas, G.; Roschger, P.; Kappe, T. Molecules 2001, 6, 338-352.
Watters, W. H.; Ramachandran, V. N. J. Chem. Research (S) 1997, 184-185; J. Chem. Research (M) 1997, 1201-1215.
O’Donnell, F.; Smyth, T. J. P.; Ramachandran, V. N.; Smyth, W. F. Inter. J. Antimicrob. Agents 2010, 35, 30-38.
Kammerer, F. J.; Gebert, U.; Alpermann, H .G. U. S. Pat. 1981, US 04 258,046; Chem. Abstr. 1982, 95, 22612s.
(a) Kappe, T.; Aigner, R.; Hohengassner, P.; Stadlbauer, W. J. Prakt Chem./Chem.-Ztg. 1994, 336, 596-601; (b) Kappe, T. Farmaco 1999, 54, 309-315.
Abass, M.; Othman, E. S. Synth. Commun. 2001, 31, 3361-3376.
Ibrahim, S. S.; Abdel-Halim, A. M.; Ismail, M. M.; Othman, E. S. Indian J. Heterocycl. Chem. 1994, 4, 125-130; Chem. Abstr. 1995,
, 143665q.
Mohamed, E. A.; Gabr, Y.; Ismail, M. M.; Abass, M. An. Quím. 1995, 91, 579-584.
Bowman, R. E.; Campbell, A.; Tanner, E. M. J. Chem. Soc. 1959, 444-447.
Kappe, T.; Ajili, S.; Stadlbauer, W. J. Heterocycl. Chem. 1988, 25, 463-468.
Ibrahim, S. S.; Allimony, H. A.; Othman, E. S. Chem. Pap. 1997, 51, 33-42.
Froggett, J. A.; Hockly, M. H.; Titman, R. B. J. Chem. Research (S) 1997, 30-31.
Jacquot, Y.; Refouvelet, B.; Bermont, L.; Adessi, G. L.; Leclercq, G.; Xicluna, A. Pharmazie 2002, 57, 233-237.
Refouvelet, B.; Guyon, C.; Jacquot, Y.; Girard, C.; Fein, H.; Bévalot, F.; Robert, J.-F.; Heyd, B.; Mantion, G.; Richert, L.; Xicluna, A. Eur. J. Med. Chem. 2004, 39, 931-937.
Alvim, J.; Dias, R. L. A.; Castilho, M. S.; Oliva, G.; Correa, A. G. J. Braz. Chem. Soc. 2005, 16, 763-773.
Abass, M.; Abdel-Megid, M.; Hassan, M. M. Synth. Commun. 2007, 37, 329-352.
Bosson, J. A.; Rasmussen, M.; Ritchie, E.; Robertson, A. V.; Taylor, W. C. Aust. J. Chem. 1963, 16, 480-490.
Abass, M.; Ismail, M.M. Chem. Pap. 2000, 54, 187-195.
Mohamed, E. A., Ismail, M. M.; Gabr, Y.; Abass, M. Chem. Pap.1994, 48, 285-292.
Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553-3561.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
