Article

 

Preparation and Some Reactions with 3–(Quinolin–3–yl)–3–Oxopropanoic Acid

 

Mohamed Abass,¹* Elhossain A. Mohamed,¹ Mostafa M. Ismail,¹ and Aisha S. Mayas²

 

¹ Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Postal Code 11757, Cairo, Egypt. Tel.: +201093694622. m.abass@chemist.com

² Department of Chemistry, Faculty of Education, Sana University, Sana, Yemen.

 

Received May 10, 2011.
Accepted August 25, 2011.

 

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.

Key words: Quinolin–2(1H)–one, β–Keto–carboxylic acid, Pyrano[3,2–c]quinoline, Knoevenagel condensation, heterocyclization reactions.

 

Resumen

La preparación del ácido quinolinil–3–oxopropanoico 2 se realizó por hidrólisis de la piranoquinolindiona 1 en medio acuoso alcalino. Se investigó el comportamiento químico de este β–cetoácido 2 en reacciones de nitrosación, acoplamiento con sales de diazonio, esterificación, condensación con 2,2–dimethoxyethanamine, hidrazinólisis, condensación de Knoevenagel con isatina, salicilaldehido, 3–formilquinolones y 3–formilchromonas. Muchos de los productos de estas reacciones pueden obtenerse mediante el uso ya sea de la piranoquinolindiona 1 o del β–cetoácido 2, bajo las mismas condiciones.

Palabras clave: Quinolin–2(1H)–ona, ácido β–ceto–carboxílico, pirano [3,2–c] quinolina, condensación de Knoevenagel, reacciones de heterociclización.

 

DESCARGAR ARTÍCULO EN FORMATO PDF

 

References

1. Abass, M.; Mostafa, B. B. Bioorg. Med. Chem. 2005, 13, 6133-6144.         [ Links ]

2. El–Shennawy, A. M.; Mohamed A. H.; Abass M. Medscape J. Med. 2007, 9, 15–33.         [ Links ]

3. Detsi, A.; Bouloumbasi, D.; Prousis, K. C.; Koufaki, M.; Athana–sellis, G.; Melagraki, G.; Afantitis, A.; Igglessi–Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou–Litina, D. J. Med. Chem. 2007, 50, 2450–2458.         [ Links ]

4. 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.         [ Links ]

5. Tani, M.; Harimaya, K.; Gyobu, Y.; Sasaki, T.; Takennouchi, O.; Kawamura, T.; Kamimura, T.; Harada, T. J. Antibiot. 2004, 57, 89–96.         [ Links ]

6. Snider, B. B.; Wu X. Heterocycles 2006, 70, 279–294.         [ Links ]

7. Ahvale, A. B.; Prokopcová, H.; Šefčovičová, J.; Steinschifter, W.; Täubl, A. E.; Uray, G.; Stadlbauer, W. Eur. J. Org. Chem. 2008, 563–571.         [ Links ]

8. Ukrainets, I. V.; Tkach, A. A.; Yang, L. Y. Chem. Heterocycl. Compds. 2008, 44, 1347–1354.         [ Links ]

9. Mohamed, E. A.; Ismail, M. M.; Gabr, Y.; Abass, M.; Farrag, H. A. Indian J. Chem. 1995, 34B, 21–26.         [ Links ]

10. Mohamed, E. A.; Ismail, M. M.; Gabr, Y.; Abass, M. J. Serb. Chem. Soc. 1993, 58, 737–743.         [ Links ]

11. Stadlbauer, W.; Badawey, E.; Hojas, G.; Roschger, P.; Kappe, T. Molecules 2001, 6, 338–352.         [ Links ]

12. Watters, W. H.; Ramachandran, V. N. J. Chem. Research (S) 1997, 184–185;         [ Links ] J. Chem. Research (M) 1997, 1201–1215.         [ Links ]

13. O'Donnell, F.; Smyth, T. J. P.; Ramachandran, V. N.; Smyth, W. F. Inter. J. Antimicrob. Agents 2010, 35, 30–38.         [ Links ]

14. Kammerer, F. J.; Gebert, U.; Alpermann, H .G. U. S. Pat. 1981, US 04 258,046;         [ Links ] Chem. Abstr. 1982, 95, 22612s.         [ Links ]

15. (a) Kappe, T.; Aigner, R.; Hohengassner, P.; Stadlbauer, W. J. Prakt Chem./Chem.–Ztg. 1994, 336, 596–601;         [ Links ] (b) Kappe, T. Farmaco 1999, 54, 309–315.         [ Links ]

16. Abass, M.; Othman, E. S. Synth. Commun. 2001, 31, 3361–3376.         [ Links ]

17. Ibrahim, S. S.; Abdel–Halim, A. M.; Ismail, M. M.; Othman, E. S. Indian J. Heterocycl. Chem. 1994, 4, 125–130;         [ Links ] Chem. Abstr. 1995, 123, 143665q.         [ Links ]

18. Mohamed, E. A.; Gabr, Y.; Ismail, M. M.; Abass, M. An. Quím. 1995, 91, 579–584.         [ Links ]

19. Bowman, R. E.; Campbell, A.; Tanner, E. M. J. Chem. Soc. 1959, 444–447.         [ Links ]

20. Kappe, T.; Ajili, S.; Stadlbauer, W. J. Heterocycl. Chem. 1988, 25, 463–468.         [ Links ]

21. Ibrahim, S. S.; Allimony, H. A.; Othman, E. S. Chem. Pap. 1997, 51, 33–42.         [ Links ]

22. Froggett, J. A.; Hockly, M. H.; Titman, R. B. J. Chem. Research (S) 1997, 30–31.         [ Links ]

23. Jacquot, Y.; Refouvelet, B.; Bermont, L.; Adessi, G. L.; Leclercq, G.; Xicluna, A. Pharmazie 2002, 57, 233–237.         [ Links ]

24. 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.         [ Links ]

25. Alvim, J.; Dias, R. L. A.; Castilho, M. S.; Oliva, G.; Correa, A. G. J. Braz. Chem. Soc. 2005, 16, 763–773.         [ Links ]

26. Abass, M.; Abdel–Megid, M.; Hassan, M. M. Synth. Commun. 2007, 37, 329–352.         [ Links ]

27. Bosson, J. A.; Rasmussen, M.; Ritchie, E.; Robertson, A. V.; Taylor, W. C. Aust. J. Chem. 1963, 16, 480–490.         [ Links ]

28. Abass, M.; Ismail, M.M. Chem. Pap. 2000, 54, 187–195.         [ Links ]

29. Mohamed, E. A., Ismail, M. M.; Gabr, Y.; Abass, M. Chem. Pap. 1994, 48, 285–292.         [ Links ]

30. Nohara, A.; Umetani, T.; Sanno, Y. Tetrahedron 1974, 30, 3553-3561.         [ Links ]