Synthesis of Air Stable Fused Bicyclic D4-1,2,4-oxadiazoline Platinum(II) Complexes via [2+3] Cycloadditions

Jamal Lasri

doi:10.14233/ajchem.2015.18683

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Issue Published : March 17, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Air Stable Fused Bicyclic D4-1,2,4-oxadiazoline Platinum(II) Complexes via [2+3] Cycloadditions

https://doi.org/10.14233/ajchem.2015.18683

Jamal Lasri

Department of Chemistry, Rabigh College of Science and Arts, King Abdulaziz University, P.O. Box 344 Rabigh 21911, Saudi Arabia

Corresponding Author(s) : Jamal Lasri

jlasri@kau.edu.sa, jamal.lasri@ist.utl.pt

Asian Journal of Chemistry, Vol. 27 No. 6 (2015): Vol 27 Issue 6
Article Published : March 18, 2015

Abstract

The reaction of trans-[PtCl₂(NCR)₂] [R¹ = CH₂CO₂Me (1a), R² = CH₂Cl (1b)] with pyrroline N-oxide ⁻O⁺N=CHCH₂CH₂CMe₂ (2) furnishes, via [2+3] cycloaddition, new fused bicyclic D⁴-1,2,4-oxadiazoline platinum(II) complexes trans-[PtCl₂{N=C(R)ONC(H)CH₂CH₂CMe₂}₂] (R¹ = CH₂CO₂Me (3a), R² = CH₂Cl (3b)). Compounds 3a and 3b were refluxed in CH₂Cl₂ to afford the derived ketoimine platinum(II) complexes trans-[PtCl₂{N(C(=O)(R))=CCH₂CH₂C(Me₂)NH}₂] (R¹ = CH₂CO₂Me (4a), R² = CH₂Cl (4b)), respectively, as a result of the N-O bond cleavage of the oxadiazoline ring in compound 3. All the platinum complexes were characterized by IR, ¹H and ¹³C NMR spectroscopies, ESI⁺-MS and elemental analyses.

Keywords

Nitriles Nitrones Cycloadditions Oxadiazolines N-O bond cleavage

Lasri, J. (2015). Synthesis of Air Stable Fused Bicyclic D4-1,2,4-oxadiazoline Platinum(II) Complexes via [2+3] Cycloadditions. Asian Journal of Chemistry, 27(6), 2249–2251. https://doi.org/10.14233/ajchem.2015.18683

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References

L. Kelland, Nat. Rev. Cancer, 7, 573 (2007); doi:10.1038/nrc2167.

A. Blasina, J. Hallin, E. Chen, M.E. Arango, E. Kraynov, J. Register, S. Grant, S. Ninkovic, P. Chen, T. Nichols, P. O’Connor and K. Anderes, Mol. Cancer Ther., 7, 2394 (2008); doi:10.1158/1535-7163.MCT-07-2391.

N.J. Wheate, S. Walker, G.E. Craig and R. Oun, Dalton Trans., 39, 8113 (2010); doi:10.1039/c0dt00292e.

B. Lippert, Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, Wiley-VCH, Weinheim (1999).

J. Sandercock, M.K.B. Parmar, V. Torri and W. Qian, Br. J. Cancer, 87, 815 (2002); doi:10.1038/sj.bjc.6600567.

C.P. Belani, Semin. Oncol., 31, 25 (2004); doi:10.1053/j.seminoncol.2004.11.005.

J. Reedijk, Curr. Opin. Chem. Biol., 3, 236 (1999); doi:10.1016/S1367-5931(99)80037-4.

P. Loehrer, S. Williams and L. Einhorn, J. Natl. Cancer Inst., 80, 1373 (1988); doi:10.1093/jnci/80.17.1373.

F.M. Muggia and T. Fojo, J. Chemother., 16S, 77 (2004).

E.S. Domnia, V.N. Varopayev, G.G. Skvorsov, S.M. Minakova and B.A. Cervou, Khim. Farm. Zh., 17, 700 (1983).

S. Mylonas, A. Valavanidis, K. Dimitropoulos, M. Polissiou, A.S. Tsiftsoglou and I.S. Vizirianakis, J. Inorg. Biochem., 34, 265 (1988); doi:10.1016/0162-0134(88)83004-6.

M.M. Muir, G.M. Gomez, M.E. Cadiz and J.A. Muir, Inorg. Chim. Acta, 168, 47 (1990); doi:10.1016/S0020-1693(00)88016-0.

M.M. Muir, O. Cox, L.A. Rivera, M.E. Cadiz and E. Medina, Inorg. Chim. Acta, 191, 131 (1992); doi:10.1016/S0020-1693(00)80339-4.

M.J. Bloemink, H. Engelking, S. Karentzopoulos, B. Krebs and J. Reedijk, Inorg. Chem., 35, 619 (1996); doi:10.1021/ic950584j.

F. Gümüs, F. İzgü and Ö. Algül, FABAD J. Pharm. Sci., 21, 7 (1996).

F. Gümüs and Ö. Algül, J. Inorg. Biochem., 68, 71 (1997); doi:10.1016/S0162-0134(97)00041-X.

G. Tallen, C. Morck, S.B. Gangopadhyay, B. Kangarloo, B. Krebs and J.E.A. Wolff, Anticancer Res., 20, 445 (2000).

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C. Mock, I. Puscasu, M.J. Rauterkus, G. Tallen, J.E.A. Wolff and B. Krebs, Inorg. Chim. Acta, 319, 109 (2001); doi:10.1016/S0020-1693(01)00459-5.

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J. Lasri, Polyhedron, 57, 20 (2013); doi:10.1016/j.poly.2013.04.017.

R.R. Fernandes, J. Lasri, M.F.C.G. da Silva, A.M.F. Palavra, J.A.L. da Silva, J.J.R.F. da Silva and A.J.L. Pombeiro, Adv. Synth. Catal., 353, 1153 (2011); doi:10.1002/adsc.201000909.

J. Lasri, M.F.C.G. da Silva, M.N. Kopylovich, S. Mukhopadhyay, M.A.J. Charmier and A.J.L. Pombeiro, Dalton Trans., 2210 (2009); doi:10.1039/b813996b.

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Synthesis of Air Stable Fused Bicyclic D4-1,2,4-oxadiazoline Platinum(II) Complexes via [2+3] Cycloadditions

Corresponding Author(s) : Jamal Lasri

Abstract

Keywords

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