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.
Geigy, J.R. and S-Triazolo A.G. (1968) [3,4-a] Isoquinolines, Neth Apple, Chemical Abstract, 68, 69003z.
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
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
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
Bentley, K.W. (2003) β-Phenylethylamines and the isoquinoline alkaloids, Natural Product Reports, 20, 342- 365. doi:10.1039/b111626f
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.
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
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
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
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
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
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 3.0.CO;2-X
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.
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
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
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.
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
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
El Ashry, E.H. and Kassem, A.A. (2006) Account of microwave irradiation for accelerating organic reactions, Arkivoc Xii, 1-16.
Nair, M.D. and Metha, S.R. (1967) Long range coupling in heterocyclic compounds, Indian Journal Chemical, 12B, 5.
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.
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.
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.
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
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
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
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
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.