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1 December 2006

Synthesis of 2-(2-napthylthio)-quinoline-3-carboxaldehyde as a novel complexing agent

,
and
1
Department of Biotechnology, GM Institute of Technology, Davangere-577 006, Karnataka, India
2
Department of Industrial Chemistry, School of Chemical Sciences, Kuvempu University, Shankaraghatta-577 451, Shimoga, Karnataka, India
*
Author to whom correspondence should be addressed.
Molbank2006, 2006(6), M518;https://doi.org/10.3390/M518
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Abstract

In this paper we propose the synthesis of 2-(2-napthylthio)-quinoline-3-carboxaldehyde. In addition to its synthesis we present elemental, IR, and NMR spectral analysis to characterize the molecule.

Introduction

In the last decade, much attention has been given to the organic ligands and transition metal complexes because of their biological relevance, interesting spectral and magnetic properties. The fused aromatic heterocyclic ligands and their metal complexes are being used extensively as pharmaceutical and chemotherapeutic agents [1,2,3,4]. On the other hand, quinoline and their derivatives form an interesting class of compounds which display attractive applications as pharmaceuticals [5,6,7,8] and are general synthetic building blocks, due to their chemical and biological relevance. Therefore, it was thought worthwhile to isolate and characterize some novel quinoline derivatives containing different donor atoms.

Synthesis of 2-(2-napthylthio)-quinoline-3-carboxaldehyde

Into a mixture of 2-Chloroquinoline-3-carboxaldehyde (0.958 g, 5 mmol), 2-naphthalenethiol (0.8 g, 5 mmol) and potassium carbonate (1.38 g, 10 mmol), anhydrous dimethylformamide (50 ml) was added. The mixture was heated at 80-90 oC for 2 h with constant stirring and was then cooled to room temperature. The product was separated on an alumina column (3x20 cm) using methylene chloride/acetonitrile (5:1) as eluant.
Melting point: 156-160 oC
Elemental Analysis: Calculated for C20H13NOS (315.38): C 76.16, H 4.15, N 4.44; found C 76.35, H 4.32, N 4.63.
IR (KBr, cm-1): 760 (-CSC-), 1710 (aldehyde, CHO), 1570 (C=C), 1650 (C=N), 2950 (C-H, aromatic).
1H-NMR (250 MHz, DMSO-d6): δ= 9.6 (s, 1H, -CHO), 7.4-8.6 (m, 11H, Ar-H).
13C-NMR (62.9 MHz,CDCl3): 128.9; 127; 130; 131; 149; 130; 141; 159; 147; 170; 125; 123; 125; 135; 126; 134; 129; 127; 128; 129.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

Acknowledgment

The authors gratefully acknowledge financial support from Mr. G.M. Lingaraju, Secretary, GM Institute of Technology, Davangere-577 006, Karnataka, India.

References

  1. O’Neill, P.M.; Bray, P.G.; Hawley, S.R.; Ward, S.A.; Park, B.K. Pharmacol.Ther. 1998, 77(1), 29.
  2. Foley, M.; Tilley, L. Pharmacol.Ther. 1998, 79(1), 55. [PubMed]
  3. Krogstad, D.J.; Gluzman, I.Y.; Kyle, D.E.; Oduola, A.M.; Martin, S.K.; Millhouos, W.K.; Schlesinger, P.H. Science 1987, 238, 1283. [PubMed]
  4. Wellems, T.E.; Walker-Jonah, A.; Panton, L.J. Proc.Natl.Acad.Sci.U.S.A 1991, 88(8), 3382. [PubMed]
  5. Madrid, P.B.; Wilson, N.T.; DeRisi, J.L.; Guy, K. J.Comb.Chem. 2004, 6, 437. [PubMed]
  6. Lukevics, E.; Segal, I.; Zablotskaya, A.; Germane, S. Molecules 1997, 2, 180.
  7. Kozlovski, V.I.; Vdovichenko, V.P.; Chlopicki, S.; Malchik, S.S.; Praliyev, K.D.; Zcikibayev, O.T. Pol. J.Pharmacol. 2004, 56, 767. [PubMed]
  8. Noda, N.; Yashiki, Y.; Nakatani, T.; Miyahara, K.; Du, X.M. Chem.Pharm.Bull. 2001, 49(7), 930. [PubMed][Green Version]

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