European Journal of Chemistry

Novel isoquinoline derivatives from isochromen-1,3-dione



Main Article Content

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.

1_2_134_139_800



icon graph This Abstract was viewed 1376 times | icon graph Article PDF downloaded 885 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).