Reactivity of 1-methylisoquinoline synthesis of pyrazolyl triazoloisoquinoline and thia-diazolyl isoquinoline derivatives

Hamdi M Hassaneen, Huwaida M. E Hassaneen, Yasmin Sh Mohammed

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Department of Chemistry, Faculty of Science, Cairo University, Cairo, Egypt.

DOI: 10.4236/ns.2011.38089                

Abstract

The reaction of 1-methylisoquinoline 1 with hy-drazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylacetal to give ena- minones 7 which react with hydrazonoyl halides to give pyrazolyl triazoloisoquinoline 13. Also, 1-methylisoquinoline 1 reacts with arylisothio-cyanate to give thioanilide 15 which reacts with hydrazonoyl halides to give the corresponding thiadiazolyl isoquinoline derivatives 20, 24.

Keywords

[1, 2, 4]Triazolo[3, 4-a]isoquinolines; Enaminones; Hydrazonoyl Halides; Cycloaddition Reactions; Chitosan; Thioanilides; [1, 3, 4]Thiadiazolylisoquinoline Derivatives

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Geigy, J.R. and S-Triazolo A.G. (1968) [3,4-a] Isoquinolines, Neth Apple, Chemical Abstract, 68, 69003z.
[2]	Solecka, J., Rajnisz, A. and Laudy, A.E. (2009) A novel isoquinoline alkaloid, DD-carboxypeptidase inhibitor, with antibacterial activity isolated from Streptomyces sp. 8812. Part I: Taxonomy, fermentation, isolation and biological activities, Journal Antibiotic, 6, 575-580. doi:10.1038/ja.2009.85
[3]	Maryanoff, B.E., McComsey, D.F., Costanzo, M.J., Setler, P.E., Gardocki, J.F., Shank, R.P. and Schneider, C.R. (1984) Pyrroloisoquinoline antidepressants. Potent, enantioselective inhibition of tetrabenazine-induced ptosis and neuronal uptake of norepinephrine, dopamine, and serotonin, Journal Medicine Chemical, 27, 943-946. doi:10.1021/jm00374a001
[4]	Tiwaria, R.K., Singha, D., Singha, J., Chhillarb, A.K., Chandraa, R. and Vermaa, A.K., (2006) Synthesis, antibacterial activity and QSAR studies of 1, 2-disubstituted- 6,7-dmethoxy-1, 2, 3, 4-tetrahydroisoquinolines, Europe Journal Medicine Chemical, 41, 40-49. doi:10.1016/j.ejmech.2005.10.010
[5]	Bentley, K.W. (2003) β-Phenylethylamines and the isoquinoline alkaloids, Natural Product Reports, 20, 342- 365. doi:10.1039/b111626f
[6]	Fül?p, F., Lazar, L., El-Gharib, M.S.A. and Bernáth, G. (1990) Saturated heterocycles. Part 166. Synthesis of 1, 5, 6, 10b-tetrahydro-1, 2, 4-triazolo [3,4-a] isoquinoline, Pharmazie, 45, 60-61.
[7]	Ito, S., Kakehi, A., Matsuno, T. and Yoshida, J. (1980) The preparation of 3-phenyl [1,2,4] triazolo [4,3-a] pyridines and their Benzologs from N-(phenylsulfonyl) benzohydazonoyl chloride and pyridines, Bull Chemical Socience Japenese, 53, 2007-2011. doi:10.1246/bcsj.53.2007
[8]	Hassaneen, H.M., Abdallah, T.A. and Awad, E. (2009) A facile access for synthesis of novel isoquiunoline-based heterocycles, Heterocycles, 78, 1507-1522. doi:10.3987/COM-09-11648
[9]	Abdallah, T.A., Abdelhadi, H.A. and Hassaneen, H.M. (2002) Reactivity of 1-Methylisoquinoline. Synthesis of 2-(1-Isoquinolinemethylidene)-1, 3, 4-Thiadiazole Derivatives, Phosphorus Sulfur and Silicon, 177, 59-66. doi:10.1080/10426500210218
[10]	Elwan, N.M., Abdelhadi, H.A. and Hassaneen, H.M. (1996) Synthesis of [1,2,4] triazolo [3,4-a] isoquinolines and pyrrolo [2,1-a] Isoquinolines using α-keto hydrazonoyl halides, Tetrahedron, 52, 3451-3456. doi:10.1016/0040-4020(96)00024-5
[11]	Abdallah, T.A., Hassaneen, H.M. and Abdelhadi, H.A. (2009) Synthesis of tetra- and penta- heterocyclic compounds incorporated isoquinoline moiety, Heterocycles, 78, 373-378. doi:10.3987/COM-08-11481
[12]	Awad, E.M., Elwan, N.M., Hassaneen, H.M., Linden A. and Heimgartner, H. (2002) New routes to fused isoquinoline, Helvetica Chimica Acta, 85, 320-331. doi:10.1002/1522-2675(200201)85:1<320::AID-HLCA320>3.0.CO;2-X
[13]	Al-matar, H.M., Khalil, K.D., Meier, H. and Elnagdi, M.H. (2008) Chitosan as heterogeneous catalyst in Michael additions: The reaction of cinnamonitriles with active methyls, active methylenes and phenols, Arkivoc Xvi, 288-301.
[14]	Guibal, E. (2005) Heterogeneous catalysis on chitosan-based materials: a review, Progress in Polymer Science, 30, 71-109. doi:10.1016/j.progpolymsci.2004.12.001
[15]	Bollini, M., Gonzalez, M. and Bruno, A. (2009) Microwave-assisted rapid and efficient synthesis of C-alkyl imidazoisoquinolinone derivatives, Tetrahedron Letters, 50, 1507-1509. doi:10.1016/j.tetlet.2009.01.083
[16]	Andrade, C.K.Z., Barreto, A.S. and Silva, W.A. (2008) Microwave assisted solvent-, support- and catalyst-free synthesis of enaminones, Arkivoc Xii, 226-232.
[17]	Lidstrom, P.J., Tierney, J., Wathey, B. and Westman, J. (2001) Microwave assisted organic synthesis—a review, Tetrahedron, 57, 9225-9283. doi:10.1016/S0040-4020(01)00906-1
[18]	Bortolini, O., D’Agostino, M., De Nino, A., Maiuolo, L., Nardi, M. and Sindona, G. (2008) Solvent-free, microwave assisted 1,3-cycloaddition of nitrones with vinyl nucleobases for the synthesis of N,O-nucleosides, Tetrahedron, 64, 8078-8081. doi:10.1016/j.tet.2008.06.074
[19]	El Ashry, E.H. and Kassem, A.A. (2006) Account of microwave irradiation for accelerating organic reactions, Arkivoc Xii, 1-16.
[20]	Nair, M.D. and Metha, S.R. (1967) Long range coupling in heterocyclic compounds, Indian Journal Chemical, 12B, 5.
[21]	Battersby, A.R., Openshaw, H.T. and Wood, H.C.S. (1953) The synthesis of emetine and related compounds. Part II. The synthesis of (±)-rubremetinium bromide, Journal Chemical Socience, 2463-2470.
[22]	Gomha, S.M. and Riyadh, S.M. (2009) Synthesis of triazolo [4,3-b] [1,2,4,5] tetrazines and triazolo [3,4-b] [1,3,4] thiadiazines using chitosan as ecofriendly catalyst under microwave irradiation, Arkivoc Xii, 58-68.
[23]	Hassaneen, H.M., Hassaneen, H.M.E. and Mohammed, Y.Sh. (2011) Synthesis, Reactions and Antibacterial Activity of 3-Acetyl [1,2,4] triazolo [3,4-a] isoquinoline Derivatives using Chitosan as Heterogeneous Catalyst under Microwave Irradiation, Verlag der Zeitschrift für Naturforschung, 66b, 299-310.
[24]	Dawood, K. M. (2005) Synthesis of Spiro-pyrazole-3, 3’- thiopyrano [2,3-b] pyridines and Azolo [a] pyrido [2’,3’:5,6] thiopyrano [3,4-d] pyrimidines as New Ring Systems with Antifungal and Antibacterial Activities, Journal Heterocyclic. Chemical, 42, 221-225. doi:10.1002/jhet.5570420207
[25]	Farag, A.M., Mayhoubb, A.S., Barakatb, S.E. and Bayomi, A.H. (2008) Regioselective synthesis and antitumor screening of some novel N-phenylpyrazole derivatives. Bioorganic and Medicinal Chemistry, 16, 881-889. doi:10.1016/j.bmc.2007.10.015
[26]	Komarova, E.S., Makarov, V.A., Alekseeva, G.V. and Granik, V.G. (2006) Synthesis of derivatives of a new heterocyclic system pyrazolo [3,4-b] pyrido [1’,2’:1,2] imidazo [4,5-d] pyridine, Russian Chemical Bull International Edition, 55, 735-740. doi:10.1007/s11172-006-0322-z
[27]	He, F.Q., Liu, X.H., Wang, B.L. and Li, Z.M. (2008) Synthesis and biological activities of novel bis-heterocy- clic pyrrodiazole derivatives, Heteroatom Chemical, 19, 21-27. doi:10.1002/hc.20369
[28]	Amer, F.A., Hammouda, M., El-Ahl, A.S. and Abdelwahab, B.F. (2007) Synthesis of Important New Pyrrolo [3,4-c] pyrazoles and Pyrazolyl-Pyrrolines from Heterocyclic β-Ketonitriles, Journal Chinese Chemical Socience, 54, 1543-1552.