Palladium-Catalyzed Sonogashira Synthesis of Alkynyl Derivatives of Quinoline-5, 8-Dione

Authors

  • James A. Ezugwu UNIVERSITY OF NIGERIA, NSUKKA
  • Mercy A. Ezeokonkwo
  • Sunday N. Okafor
  • Evelyn U. Godwin-Nwakwasi
  • F. N. Ibeanu

Keywords:

Alkynylquinoline-5, 8-diones, Palladium Catalysis, Sonogashira protocol, Terminal alkynes.

Abstract

The synthesis of various alkynylquinoline-5,8-diones is reported. The intermediate 6,7-dibromoquinoline-5,8-dione was obtained by nitrosation of 8-hydroxyquinoline, followed by reduction and subsequent bromination and oxidation. The coupling reaction of 6,7-dibromoquinoline-5,8-dione with various terminal alkynes via Palladium catalysis gave the alkynylquinoline-5,8-diones in good to excellent yields (50-85% ). The chemical structures of the products were confirmed using spectroscopic methods, which include UV/Visible spectrophotometer, Fourier Transform-Infrared (FT-IR) Spectroscopy, 1H and 13C-NMR Spectroscopy. In vitro antimicrobial activity screening carried out on the compounds against bacterial strains: Escherichia coli 1, Escherichia coli 12, Staphylococcus aureus, Klebsiella pneumonia and Pseudomonas aeroginosa, showed that the synthesized compounds have significant activities (MIC= 0.15-3.20), against the tested organisms. However, compound 5e did not inhibit the growth of Pseudomonas aeroginosa.

Author Biography

James A. Ezugwu, UNIVERSITY OF NIGERIA, NSUKKA

PURE AND INDUSTRIAL CHEMISTRY. Ph.D Student

References

. Behforouz, M.; Haddad, J.; Cai, W.; Gu, Z. Chemistry of quinoline-5,8-diones. J.org.chem., 63,343-346, 1998.

. Harinath,B.B.; Subba Rao, N. V. Synthesis and fungistatic activity of 5:6- and 5:8- quinoline quinine Sym. Syn Heterocyclic compounds physiol interest, Indian patent 1033af, 069, 1964 ( pub. 1996).

. Schellhammer, C.W.; petterson, S. Derivatives of 5,8-quinoline quinines. Chem. Abstr, Ann, 624,108-119, 53,15211e, 1960.

. Pratt, Y. L.; Drake, N.L. Quinoline quinine V, 6-Chloro- and 7-Chloro-5,8-quinolne quinine. J.Am.Chem.Soc., 82,1155-1161, 1960.

. Brandsma. L. Synthesis of Acetylene, Allenes and Cumulenes: Methods and Techniques: Elsever oxford, 293, 2004.

. Brandsma. L.; Vasilevsky, S.F.; Verkruijase. H.D. Application of transition metal catalysts in organic synthesis, springer Berlin, 179-225, 1998.

. (a). Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient Syntheses of acetylenes catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron lett.,50, 4467-4470, 1975.

(b). Cassar. L. Palladium catalyzed synthesis of aryl heterocyclic and vinyl acetylene derivatives. J.organomett.

chem., 93, 253-257, 1975.

(c).Dieck, H.; Heck, F. Palladium catalyzed synthesis of aryl heterocyclic and vinyl acetylene derivatives. J.organomett. chem., 93, 259-263, 1975.

. Thorand, S.; Krause, N.J. Poly( arylene ethynylenes) from synthesis to applications. J.org.chem., 1998, 63, 8551-8553, 1998.

. Elangonvan, A.; Wang, Y.H.; Ho, T.I. Sonogashira coupling reaction with diminished homo-coupling. Org.lett., 5, 1841-184, 2003.

. Rossi, R.; Carpita, A.; Bigeili, C. Tetrahedron, 26,523, 1985.

. Bohm. V.P.M.; Hermann, W.A. Eur.j.org.chem., 6, 3679, 2000.

. Godwin-Nwakwasi, E.U. Utility of Buchwald-Hartwig, Mizoroki-Heck and Suzuki- Miyaura cross-coupling reaction in the synthesis of Non-linear Polycylic phenothiazine derivatives: Ph.D Thesis, university of Nigeria.2011.

. Nnabugwu, M.A. Synthesis of some New Aza Analogues of Angular phenothiazines of industrial interest; Ph.D.Thesis, university of Nigeria, Nsukka, 2009.

. Jun-Heng, L.; Xang, Y.; Xie, Y. Modified palladium-catalyzed Sonogashira cross coupling rractions under copper-, Amine- and solvent-free conditions. J.Org.Chem.; 71,379-381, 2006.

. Perecz, C.; Pauli, M.; Bazergue, P. Antibiotic Assay by the agar-well diffusion method. Acta Biologiae et Medicine Experimental, 15,113-115, 1990.

Onoabedje, E. A.; Okoro, U. C.; Sarka, A.; Knight, D. W.Synthesis and structure of new alkynyl derivatives of phenothizine and phenoxazine. J. Sulfur Chem.; 37:3;269-281, 2016.

. Tsuji J., Palladium reagents and catalysis; new perspective for 21st century chemist. Chichester:Wiley, 2014.

. Thomson. R.H. Studies in the juglone series. 1. Some halogen derivatives and their reaction with aniline. J.Org. Chem.; 13, 377, 1948.

Chinchilla, R.; Najera, C. The Sonogashira reaction: A Booming methodology in synthetic organic chemistry. Chem.Rev., 107, 874-922, 2007.

. Geliman, D.; Buchwald, S.L. Efficient Palladium-catalyzed coupling reactions of aryl chloride and Tosylates with alkynes: use of a copper cocatalyst inhibits the Reaction. Angew.Chem. Int. Ed.; 42, 5993-5996, 2003.

. Reetz, M. T.; De Vries, J.G. The role of TBA- in the cross-coupling. Adv. Mater. 11, 773, 2004.

. Urganokar, S.; Verkade. J.G. Palladium-catalyzed Sonogashira cross-coupling reactions under ligand and copper-free condition. J.Org. Chem.; 69, 5752,2004.

. Mori, A.; Kawashima, J.; Shimada, T.; Suguro, M.; Hirabayashi, K.; Nishihara, Y. TBAF as an activator for the palladium-catalyzed Sonogashira reaction. J.Org.Lett.; 2, 2935, 2000.

. Witulski, B.; Azeon, J.R.; Alayrac, C.;Amuatu, A.; Collot, V.; Rault,S. Sequential Sonogashira and Suzuki cross-coupling reactions in the indole and indazole series. Synthesis, 5, 771, 2005.

. Obasi L. N.; Ukoha P. O.; Chah K. F. Synthesis of some sulphonyl derivatives of aminothiazole and

antimicrobial screening, 35:1, 190-193, 2010.

Downloads

Published

2017-12-22

How to Cite

Ezugwu, J. A., Ezeokonkwo, M. A., Okafor, S. N., Godwin-Nwakwasi, E. U., & Ibeanu, F. N. (2017). Palladium-Catalyzed Sonogashira Synthesis of Alkynyl Derivatives of Quinoline-5, 8-Dione. Asian Journal of Applied Sciences, 5(6). Retrieved from https://ajouronline.com/index.php/AJAS/article/view/4987