SYNTHESIS AND REACTIONS OF SOME NEW MORPHOLINYLPYRROLYL TETRAHYDROTHIENO[2,3-c] ISOQUINOLINE
DOI:
https://doi.org/10.24297/jac.v10i3.6659Keywords:
Tetrahydrothienoisoquinoline, Pyrrole, Pyrazole, Triazole, SynthesisAbstract
Hydrazinolysis of ethyl-5-morpholin-4-yl-1-(1H-pyrrol-1-yl)-6,7,8,9-tetrahydrothieno[2,3-c]iso- quinoline-2-carboxylate afforded the corresponding carbo- hydrazide which upon condensation with aromatic aldehydes, acetyl acetone and/ or carbon disulfide gave N- arylidinecarbohydrazide, dimethylpyrazolyl methanone, [1,3,4]oxadiazole-2-thiol and its ethyl ester derivatives respectively. Diazotization of the carbohydrazide with nitrous acid afforded the corresponding carboazide which was used for synthesis of carbamates and substituted carboxamides. Boiling of the carboazide in dry xylene afforded the pyrazinone compound which was used for synthesis of other heterocycles containing pyrrolopyrazinothinoisoquinoline moeity.
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References
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[4] Iwasa, K., Moriyasu, M., Tachibana, Y., Kim, H.S., Wataya, Y., Wiegrebe, W., Bastow, K. F., Cosentino, L. M., Kozuka, M., and Lee, K.H. Bioorg. Med. Chem. 2001, 9, 2871–2884. Simple Isoquinoline and Benzylisoquinoline Alkaloids as Potential Antimicrobial, Antimalarial, Cytotoxic, and Anti-HIV Agents
[5] Cheng, P., Huang, N., Jiang, Z. Y., Zhang, Q., Zheng, Y. T., Chen, J. J., Zhang, X. M., and Ma, Y.B. Bioorg. Med. Chem. Lett. 2008, 18, 2475– 2478. 1- Aryltetrahydroisoquinoline analogs as active anti-HIV agents in vitro.
[6] Pham, V.C., Ma, J., Thomas, S. J., Xu, Z., and Hecht, S.M. J. Nat. Prod. 2005, 68, 1147– 1152. Alkaloids from Alangium javanicum and Alangium grisolleoides that Mediate Cu2+- Dependent DNA Strand Scission.
[7] Naito, R., Yonetoku, Y., Okamoto, Y., Toyoshima, A., Ikeda, K., and Takeuchi, M. J Med. Chem. 2005, 48, 6597– 6606.Synthesis and Antimuscarinic properties of Quinclidin-3-yl- 1,2,3,4-Tetrahydroisoquinoline-2-carboxylate Derivatives as Novel Muscarinic Receptor Antagonists
[8] Leeson, P. D., Carling, R. W., Moore, K. W., Moseley, A. M., Smith, J. D., Stevenson, G., Chan, T., Baker, R., Foster, A. C., Grimwood, S., Kemp, J. A., Marshall, G. R., and Hoogsteen, K., J. Med. Chem. 1992, 35, 1954-1968. 4-Amido-2 carboxytetrahydroquinolines. Structure-activity relationships for antagonism at the glycine site of the NMDA receptor.
[9] Nagata, R., Tanno, N., Kodo, T., Ae, N., Yamaguchi, H., Nishimura, T., Antoku, F., Tatsuno, T., Kato, T., Tanaka, Y. and Nakamura, M., J. Med. Chem. 1994, 37, 3956-3968. Tricyclic Quinoxalinediones:5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline- 2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor.
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[11] Stanton, J. L. and Ackerman, M. H. J. Med. Chem. 1983, 26, 986-989. Synthesis and anticonvulsant activity of some tetracyclic indole derivatives.
[12] Shutske, G. M., and Kapples, J. U.S. Pat., 1998, 4, 753, 950; Chem. Abstr. 1988, 109, 128990j.
[13] McCarthy, J. R. and Winder, P. J. Eur. Pat. 1985, 126, 487, Chem. Abstr., 1985, 102, 135078r.
[14] Hashimoto K., Inoe, M., Tomoyasu, T., Kamisako, T., Sugimoto, Y. and Kuwabara, T., Jap. Pat., 1994, 06, 92, 963; Chem Abstr., 1994, 121, 157630v. [15] Sauter, F., Jordis, U., Tanyolac, S. and Martinek, P. Arch. Pharm. 1988, 321, 241-246. Synthesen neuer Chinolon-Chemotherapeutika, 2. Mitt.: Thieno[3,2-g]chinolin-und [1]Benzothieno-[5,6,7-ij]chinolizincarbonsäurederivate.
[16] Wagner, G., Vieweg, H. and Leistner, S. Phramazie 1993, 48, 576-578.
[17] Kamal El-Dean, A. M., Radwan, Sh. M. and Zaki, R.M., J. Chin. Chem. Soc. 2008, 55, 1-10. Synthesis of Morphlinotetrahydrothieno[2,3-c]isoquinolines.
[18] Kamal, A.M., Radwan, Sh.M., and Zaki, R.M. J. Chem. Res. 2010, 34, 596-602 Reactions of 1-amino-5-morpholino-6,7,8,9-tetrahydrothieno [2,3-c]isoquinoline-2-carbonitrile.
[19] Kamal, A.M, Radwan, Sh.M., and Zaki, R. M. Eur. J. Med. Chem. 2011, 46, 567-578. Synthesis and biological activity of pyrazolothienotetrahydroisoquinoline and [1,2,4]triazolo[3,4-a]thienotetrahydroisoquinoline derivatives.
[20] Kamal, A.M., Radwan, Sh.M. and Zaki, R. M. J. Chin. Chem. Soc. 2011, 58, 544-554. Synthesis and Reactions of 1-Amino-5-morpholin-4-yl-6,7,8,9-tetrahydro thieno[2,3-c]isoquinoline.
[21] Zaki, R.M., Kamal El-Dean, A.M.and Radwan, Sh.M. Afindad 2012, LXVII, 424-434. Synthesis and reactions of novel thienotetrahydroisoquinoline compounds.
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Published
2014-07-31
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Zaki, R. M., Kamal El-Dean, A. M., & Radwan, S. M. (2014). SYNTHESIS AND REACTIONS OF SOME NEW MORPHOLINYLPYRROLYL TETRAHYDROTHIENO[2,3-c] ISOQUINOLINE. JOURNAL OF ADVANCES IN CHEMISTRY, 10(3), 2512–2523. https://doi.org/10.24297/jac.v10i3.6659
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