European Journal of Chemistry

Novel isoquinoline derivatives from isochromen-1,3-dione



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Mahmoud Refaee Mahmoud
Manal Mohamed El-Shahawi
Eman Abd El-Fattah El-Bordany
Fatma Saber Mohamed Abu El-Azm

Abstract

A number of novel isoquinoline derivatives have been synthesized using the readily obtainable (E)-4-(3,4-dimethoxybenzylidene)-4H-isochromene-1,3-dione, 2, via the reaction with different nitrogen nucleophiles such as cyanoethanoic hydrazide, cyclohexylamine, 2-aminothiophenol and p-toluenesulfonohydrazide. Furthermore, the reactivity of 2 towards thiophenol, and ethylcyanoacetate has been investigated.

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Mahmoud, M. R.; El-Shahawi, M. M.; El-Bordany, E. A. E.-F.; Abu El-Azm, F. S. M. Novel Isoquinoline Derivatives from Isochromen-1,3-Dione. Eur. J. Chem. 2010, 1, 134-139.

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References

[1]. Alien, G. R.; Littell, R.; McEvoy, F. J.; Sloboda, A. E. J. Med. Chem. 1972, 15, 934-937.
doi:10.1021/jm00279a014
PMid:5051012

[2]. Barry, R. P. Chem. Rev. 1964, 64, 229-260.
doi:10.1021/cr60229a002

[3]. Billingam, M. E. G. J. Pharmacol. 1981, 72, 523-526.

[4]. Kovacs, T.; Sonnenbichler, J. Liebigs Ann. Rcl. 1997, 1, 211-212.
doi:10.1002/jlac.199719970130

[5]. Mali, R. S.; Babu, K.N. J. Org. Chem. 1998, 63, 2488.
doi:10.1021/jo971622e
PMid:11672109

[6]. Noguchi, S.; Kishimoto, S.; Minamida, I.; Obayashi, M. Chem. Pharm. Bull. 1974, 22, 529-536.

[7]. Stadler, M.; Anke, H.; Sterner, O. J. Antibio. 1995, 48, 261-266.

[8]. Chinworrungs, M.; Kittakoop, P.; Isaka, M.; Chanphen, R.; Anicharoen, M.; Thebtaranonth, Y. J. Chem. Soc., Perkin Trans 1 2002, 22, 2473-2476.

[9]. Rama, N. H.; Iqbal, R.; Zamani, K. J. Chem. Soc. Pak. 1998, 20, 62-65.

[10]. Stephen W. P.; Koslowski, M. C. Tetrahedron Lett. 2001, 42, 3567-3570.
doi:10.1016/S0040-4039(01)00524-X

[11]. Hajipour, A.; Mallakpour, S.; Imanzadeh, G. Indian J. Chem. 2001, 40B, 250-251.

[12]. Karina, F.; Devienna, M.; Sela Raddi, G.; Eliana, A.; Varand, Z. Z. Naturforsch 2002, 57, 85-88.

[13]. Gitto, R.; Barreca, M.; Francica, E.; Caruse, R.; Deluea, L.; Russo, E.; Desarro, G.; Chimirri, A. Arkivoc 2004, 5, 170-180.

[14]. Azizian, J.; Mohammadi, A. A.; Karami, A. R.; Mohammadizadeh, M. R. A. J. Org. Chem. 2005, 70, 350-352.
doi:10.1021/jo049138g
PMid:15624947

[15]. Kandinska, M. I.; Kozekov, I. D.; Palamareva, M. D. Molecules 2006, 11, 403-414.
doi:10.3390/11060403
PMid:17962773

[16]. Kane, T. R.; Ly, C. Q.; Kelly, D.E.; Denner, J. M. J. Comb. Chem. 2004, 6, 564-572.
doi:10.1021/cc020105t
PMid:15244418

[17]. Kim, H. J.; Yoon, U. C.; Young, S. Y.; Park, N. S.; Cedeistrom, E.M.; Marriano; P. S. J. Org. Chem. 1998, 63, 860-863.
doi:10.1021/jo971705v
PMid:11672083

[18]. Kozekov, I. D.; Koleva, R. I.; Palamareva, M. D. J. Heterocyclic Chem. 2002, 39, 229-236.
doi:10.1002/jhet.5570390134

[19]. Stoyanova, M. P.; Kozekov, I. D.; Palamareva, M.D. J. Heterocyclic Chem. 2003, 40, 795-803.
doi:10.1002/jhet.5570400508

[20]. Yadav, J. S.; Reddy, B. V. S.; Saritha Raj, K.; Prasad, A. R. Tetrahedron 2003, 59, 1805-1809.
doi:10.1016/S0040-4020(03)00076-0

[21]. Zalan, Z.; Martinek, T. A.; Lazar, L.; Fulop, F. Tetrahedron 2003, 59, 9117-9125.
doi:10.1016/j.tet.2003.09.062

[22]. Coelho, F.; Veronese, D.; Lopes, E. C. S.; Rossi, R. C. Tetrahedron Lett. 2003, 44, 5731-5735.
doi:10.1016/S0040-4039(03)01307-8

[23]. Shaabani, A.; Soleimani, E.; Khavasi, H. R. Tetrahedron Lett. 2007, 48, 4743-4747.
doi:10.1016/j.tetlet.2007.05.019

[24]. Knolker, H. J.; Agarwal, S. Tetrahedron Lett. 2005, 46, 1173-1175.
doi:10.1016/j.tetlet.2004.12.066

[25]. Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669-1730.
doi:10.1021/cr010212u
PMid:11996547

[26]. Mahmoud, M. R.; El-Shahawi, M. M.; Farahat, S. E. J. Chem. Res. 2008, 2, 86-88.

[27]. Mahmoud, M. R.; El-Shahawi, M. M.; Farahat, S. E. J. Chem. Res. 2008, 1, 59-60.

[28]. Mahmoud, M. R.; El-Shahawi, M. M.; El-Bordany, E. A. A.; Abu El-Azm, F.S. M. Synth. Commun. 2010, 40, 666-676.
doi:10.1080/00397910903009463

[29]. Morgenstern, A. P.; Schuitj, C.; Nauta, W. T. J. Chem. Soc. Chem. Commun. 1969, 7, 321-322.

[30]. Morgenstern, A. P.; Schuitj, C.; Nauta, W. T. J. Chem. Soc. 1971, 3706-3712.

[31]. Boyed, G. V.; Monteil, R. L. J. Chem. Soc. Perkin Trans. 1 1978, 11, 1338-1350.

[32]. Sausen, G. N.; Engelhardt, V. A.; Middleton, W. J. J. Am. Chem. Soc. 1958, 80, 2815-2822.
doi:10.1021/ja01544a057

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