European Journal of Chemistry

The chemical reactivity of naphthols and their derivatives toward α-cyanocinnamonitriles and ethyl α-cyanocinnamates: A review of synthesis, reactions and applications of naphthopyrano



Main Article Content

Ashraf Hassan Fekry Abd El-Wahab
Hany Mostafa Mohamed
Ahmed Mohamed El-Agrody
Ahmed Hammam Bedair

Abstract

This review deals with synthesis and reactions of some naphthopyrano derivatives and their applications. The main purpose of this review is to present a survey of literatures on the reactivity of naphthols and their derivatives toward α-cyanocinnamonitrile or ethyl α-cyanocinnamate derivatives and the reactions of β-enaminonitriles and β-enaminoesters with different electrophiles followed by nucleophilic reagents. Some of these reactions have been applied successfully to the synthesis of biologically important compounds.

4_4_467_483

icon graph This Abstract was viewed 3202 times | icon graph Article PDF downloaded 1604 times

How to Cite
(1)
El-Wahab, A. H. F. A.; Mohamed, H. M.; El-Agrody, A. M.; Bedair, A. H. The Chemical Reactivity of Naphthols and Their Derivatives Toward α-Cyanocinnamonitriles and Ethyl α-Cyanocinnamates: A Review of Synthesis, Reactions and Applications of Naphthopyrano. Eur. J. Chem. 2013, 4, 467-483.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Singh, R. G.; Chauhan, S. M. S. Chem. Biodivers. 2004, 1(9), 1241-1264.
http://dx.doi.org/10.1002/cbdv.200490088
PMid:17191903

[2]. Costa, S. M. O.; Lemos, T. L. G.; Pessoa, O. D. L.; Pessoa, C.; Montenegro, R.; Braz-Filho, R. J. Nat. Prod. 2001, 64, 792-795.
http://dx.doi.org/10.1021/np0005917

[3]. Itokawa, H.; Qiao, Y.; Takeya, K. Phytochemistry 1989, 28, 3465-3468.
http://dx.doi.org/10.1016/0031-9422(89)80365-6

[4]. The Ministry of Public Health, Pharmacopeia of the People's Republic of China; Guangdong Science and Technology Press: Guangzhou, P. R. China, 1992; pp. 179.

[5]. Inoue, K.; Shiobara, Y.; Nayeshiro, H.; Inouye, H.; Wilson, G.; Zenk, M. H. Phytochemistry 1984, 23, 307-311.
http://dx.doi.org/10.1016/S0031-9422(00)80323-4

[6]. Kawasaki, Y.; Goda, Y.; Yoshihira, K. Chem. Pharm. Bull. 1992, 40, 1504-1509.
http://dx.doi.org/10.1248/cpb.40.1504
PMid:1394669

[7]. Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67, 127-131.
http://dx.doi.org/10.1055/s-2001-11498
PMid:11301857

[8]. Itokawa, H.; Mihar, T.; Takeya, K. Chem. Pharm. Bull. 1983, 31, 2353-2358.
http://dx.doi.org/10.1248/cpb.31.2353

[9]. Gutpa, P. P.; Srimal, R. C.; Verma, N.; Tandon, J. S. Pharm. Biol. 1999, 37, 46-49.
http://dx.doi.org/10.1076/phbi.37.1.46.6322

[10]. Gil, S. J.; Dong, S. L.; Dong, C K.; Yurngdong, J.; Jong, K. S.; Seung, H. L; Youn, C. K. Eur. J. Pharmacol. 2011, 654, 226-234.
http://dx.doi.org/10.1016/j.ejphar.2010.12.027
PMid:21236252

[11]. Fathy, A. E., Ashraf, H. F. A.; Gameel, A. M. E.; Mostafa, M. K. Acta Pharm. 2004, 54, 13-26.

[12]. Ashraf, H. F. A. Pharmaceuticals 2012, 5, 745-757.
http://dx.doi.org/10.3390/ph5070745

[13]. El-Agrody, A. M.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H.; El-Sayed, E. M.; El-Ghareab, K. A. Acta Pharm. 2000, 50, 111-120.

[14]. Wang, X. S.; Yang, G. S.; Zhao, G. Tetrahedron Asymmetr. 2008, 19, 709-714.
http://dx.doi.org/10.1016/j.tetasy.2008.02.018

[15]. Wang, X. S.; Zheng, C. W.; Zhao, S. L.; Chai, Z.; Zhao, G.; Yang, G. S. Tetrahedron Asymmetr. 2008, 19, 2699-2704.
http://dx.doi.org/10.1016/j.tetasy.2008.11.025

[16]. Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. J. Chin. Chem. Soc. 2008, 55, 659-662.

[17]. Pasha M. A.; Jayashankara, V. P. Indian J. Chem. B 2007, 46, 1328-1331.

[18]. Balalaie S.; Ramezanpour S.; Bararjanian M.; Gross J. H. Synth. Commun. 2008, 38(7), 1078-1089.
http://dx.doi.org/10.1080/00397910701862865

[19]. Kai, G.; Hua, L. W.; Dong, F.; Zu, L. L. Catal. Commun. 2008, 9(5), 6550-6553.

[20]. Reza, M. N. J.; Ali S. Mol. Divers. 2010, 14, 473-477.
http://dx.doi.org/10.1007/s11030-010-9246-5
PMid:20373141

[21]. Sanny, V.; Suman, L. J. Tetrahedron Lett. 2012, 53(45), 6055-6058.
http://dx.doi.org/10.1016/j.tetlet.2012.08.118

[22]. Srihari, P.; Gangana, B.; Rajendrapasad K.; Dinesh C. B.; Yadav, J. S. Indian J. Chem. B 2011, 50, 1755-1761.

[23]. Hong, J. W.; Xiao, Q. R.; Yan, Y. Z.; Zhan, H. Z. J. Braz. Chem. Soc. 2009, 20, 1939-1943.
http://dx.doi.org/10.1590/S0103-50532009001000025

[24]. Saman, D.; Reza, S.; Majid, V.; Hamid, R. M. Chinese Chem. Lett. 2012, 23, 253-256.
http://dx.doi.org/10.1016/j.cclet.2011.11.025

[25]. Hossein, E.; Gholam, H. Z.; Reza, S.; Saman, D. Heterocycl. Commun. 2012, 18(2), 67-70.

[26]. Kumar, B. S.; Srinivasulu, N.; Udupi, R. H.; Rajith, B.; Thirupathi, R. P. Y.; Narsimha, R. P. Russian J. Org. Chem. 2006, 42, 1813-1815.
http://dx.doi.org/10.1134/S1070428006120098

[27]. Shestopalov, A. M.; Emelianov, Y. M.; Nesterov, V. N. Russ. Chem. Bull. Int. Edit. 2002, 51, 2238-2243.
http://dx.doi.org/10.1023/A:1022135402451

[28]. Mohammad, G. D.; Mohammad, E.; Ali, M. Tetrahedron 2013, 69, 1074-1085.
http://dx.doi.org/10.1016/j.tet.2012.11.068

[29]. Farahnaz, K. B.; Sadeghi, M. J. Korean Chem. Soc. 2013, 57(3), 357-360.
http://dx.doi.org/10.5012/jkcs.2013.57.3.357

[30]. Ahmed, M. E.; Fathy, A. E.; Hussein, A. E.; Hany, M. M.; Ahmed, H. B. Z. Naturforsch. B 2002, 57, 579-585.

[31]. Ahmed, Z. S.; Nagwa A. E.; Ahmed, M. E. J. Chem. Res. 2000, 164-166.

[32]. Ahmed, H. B.; Hussien, A. E.; Nagwa, A. E.; Kamal, A. R.; Ahmed, M. E. II Farmaco 2001, 56, 968-973.

[33]. Mogilaiah, K.; Sharath, B. H.; Vidya, K.; Shiva, K. K. Indian J. Chem. B 2010, 49, 390-393.

[34]. El-Sayed, H. E.; Mohamed, E. E.; Mohamed, H. E.; Hamdy, H. A.; Wedad, M. A. A.; Yasser, M. B. Jordan J. Chem. 2009, 4, 223-231.

[35]. Nilesh, J. T.; Manish P. P. Arkivoc 2009, 13, 363-380.

[36]. Saman, D.; Reza, S. J. Adv. Sci. Res. 2011, 2(3), 73-76.

[37]. Fadda, A. A.; Hala, M. R.; Zaki M. E. A. Molecules 2000, 5, 701-709.
http://dx.doi.org/10.3390/50500701

[38]. Kidwai, M.; Kumar, P. J. Chem. Res. S. 1997, 5, 178-179.
http://dx.doi.org/10.1039/a700516d

[39]. Issa, Y.; Mohammad, A. A.; Abdolali, A.; Zinatossadat H. Tetrahedron 2003, 59, 1289-1292.
http://dx.doi.org/10.1016/S0040-4020(03)00030-9

[40]. El-Agrody, A. M.; Emam, H. A.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery A. H. J. Chem. Res. S 1997, 320-321.

[41]. Mostafa, M. K.; Ashraf, H. F. A.; Fathy, A. E.; Ahmed, M. E. Il Farmaco 2002, 57, 715-722.
http://dx.doi.org/10.1016/S0014-827X(02)01263-6

[42]. Abdullah, G. A.; Ahmad, I.; Ahmed, M. E. J. Mol. Struc. 2012, 1018, 171-175.
http://dx.doi.org/10.1016/j.molstruc.2012.03.018

[43]. Lu, C.; Exu, J. H.; Eyi, Q. L.; Mei, Y. Z. E.; Wen. J. Z. E. Monatsh. Chem. 2009, 140, 45-47.
http://dx.doi.org/10.1007/s00706-008-0008-3

[44]. Zhongqiang, Z.; Fangyun, Y.; Lamei, W.; Aiqing, Z. Chem. Sci. Trans. 2012, 1(1), 57-60.
http://dx.doi.org/10.7598/cst2012.125

[45]. Jitender, M. K.; Bhaskara, N.; Pooja, S. Tetrahedron 2010, 66(30), 5637-5641.
http://dx.doi.org/10.1016/j.tet.2010.05.082

[46]. Ramadan, A. M.; Kamal, U. S. J. Heterocyclic Chem. 2009, 46(2), 149-151.
http://dx.doi.org/10.1002/jhet.13

[47]. Mandar, P. S.; Siddheshwar, K.; Shriniwas, D. S. Tetrahedron Lett. 2009, 50(6), 719-722.
http://dx.doi.org/10.1016/j.tetlet.2008.11.114

[48]. Maggi, R.; Ballini, R.; Sartori, G.; Sartorio, R. Tetrahedron Lett. 2004, 45(11), 2297-2299.
http://dx.doi.org/10.1016/j.tetlet.2004.01.115

[49]. Wang, X. S.; Shi, D. Q.; Yu, H. Z.; Wang, G. F.; Tu, S. J. Synth. Commun. 2004, 34, 509-514.
http://dx.doi.org/10.1081/SCC-120027291

[50]. Pandey, V. K.; Tusi, Z.; Tusi, S.; Joshi, M. N. Chem. Sci. J. 2012, 72, 1-6.
http://dx.doi.org/10.1016/j.ces.2011.12.040

[51]. Raafat, M. S. Arkivoc 2006, 14, 59-67.

[52]. Maruoka, H.; Yamagata, K.; Yamazaki, M. Liebigs Ann. Chem. 1993, 1269-1271.
http://dx.doi.org/10.1002/jlac.1993199301207

[53]. Veronese, A. C.; Gandolfi, V.; Basato, M.; Corain, B. J. Chem. Res. S 1988, 246-247.

[54]. Veronese, A. C.; Callegari, R.; Salah, S. A. A. Tetrahedron Lett. 1990, 31(24), 3485-3488.
http://dx.doi.org/10.1016/S0040-4039(00)97429-X

[55]. Veronese, A. C.; Callegari R.; Morelli, C. F. Tetrahedron 1995, 51(45), 12277-12284.
http://dx.doi.org/10.1016/0040-4020(95)00773-2

[56]. Li, J. R.; Zhang, L. J.; Yang, X. Q.; Li, Q.; Wang, D.; Wang, C. X.; Shi, D. X.; Zhang, Q. Chin. Chem. Lett. 2008, 19(1), 15-18.
http://dx.doi.org/10.1016/j.cclet.2007.11.003

[57]. Eman, A.; Islam, H. E. Eur. J. Chem. 2012, 3(1), 81-86.
http://dx.doi.org/10.5155/eurjchem.3.1.81-86.507

[58]. Dell, C. P.; Smith, C. W. Eur. Pat. Appl. EP 537, 949; ref. Chem. Abstr., 1993, 119, 139102d.

[59]. Brunavs, M.; Dell, C. P.; Gallagher, P. T.; Owton, W. M.; Smith C. W. Eur. Pat. Appl. EP 557, 075; Chem. Abstr., 1994, 120 106786t.

[60]. Giorgio, R.; Mario, D.; Antonio, C.; Giancarlo, G.; Giuliana, L.; Maria, G. S.; Angelo, C. Bioorgan. Med. Chem. 2003, 11, 123-138.
http://dx.doi.org/10.1016/S0968-0896(02)00307-3

[61]. Tandon, V. K.; Vaish, M.; Jain, S.; Bhakuni, D. S.; Srimal R. C. Indian J. Pharm. Sci. 1991, 53, 22-23.

[62]. Hwan, M. Y. K; Pil, R. Y.; Mun, S. S.; Jae, S. Y.; Jin, H. H.; Seung, J. J.; Young, G. K.; Kyoung, J. L.; Bong, R. C. J. Org. Chem. 2007, 72, 2088-2096.
http://dx.doi.org/10.1021/jo062341m
PMid:17316048

[63]. Wen, F. C.; Shyh, Y. L.; Li, K. H.; Ming, L. H.; Ming, J. D. J. Med. Chem. 2000, 37, 69-75.

[64]. Evelyne, R.; Charles, B.; Sebastien, M.; Gaetan, H.; Veronique, L.; Robert, G. Polym. Int. 2004, 53, 455-459.

[65]. Xavier, S.; Gaston, V.; Guillaume, S.; Jean, L. P.; Stephanie, D. J. Photoch. Photobio. A 2008, 200, 68-73.
http://dx.doi.org/10.1016/j.jphotochem.2008.04.009

[66]. Christopher, D. G.; Mark, H.; Suresh, B. K.; Matthew, M. Eur. J. Org. Chem. 2008, 2008, 2031-2034.

[67]. Bingjie, X.; Guang, W.; Xiancai, Z. J. Appl. Polym. Sci. 2011, 122, 3377-3382.
http://dx.doi.org/10.1002/app.34427

[68]. Nuran, E.; Ping, Y.; Nukhet, A. J. Chromatogr. 2001, 753, 287-282.
http://dx.doi.org/10.1016/S0378-4347(00)00560-0

[69]. Sashidhara, K. V.; Rosaiah, J. N.; Bhatia, G.; Saxena, J. K. Eur. J. Med. Chem. 2008, 43(11), 2592-2596.
http://dx.doi.org/10.1016/j.ejmech.2007.10.029
PMid:18063225

[70]. Smith, C. W.; Bailey, J. M.; Billingham, M. E. J.; Chandrasekhar, S.; Dell C. P.; Harvey A. K.; Hicks C. A.; Kingston A. E.; Wishart G. N. Bioorg. Med. Chem. Lett. 1995, 5, 2783-2788.
http://dx.doi.org/10.1016/0960-894X(95)00487-E

[71]. Bloxham J.; Dell, C. P.; Simith, C. W. Heterocycles 1994, 38, 399-409.
http://dx.doi.org/10.3987/COM-93-6594

[72]. Herman, J. P. R.; Harmans, W. R. M.; Vos, J.; Serruys, P. W. Drugs 1993, 46, 18-52.
http://dx.doi.org/10.2165/00003495-199346010-00003

[73]. Lee, P. C.; Gibbans, G. H.; Dzau, V. J. Coronary Art. Dis. 1993, 4, 254-259.
http://dx.doi.org/10.1097/00019501-199303000-00005
PMid:8269219

[74]. Wiernicki, T. R.; Bean, J. S.; Williams, A.; Wood, D.; Kauffman, R. F.; Singh J. P. J. Pharmacol. Exp. Ther. 1996, 278, 1452-1459.

[75]. Panda, D.; Singh, J. P.; Willson, L. J. Bio. Chem. 1997, 272, 7681-7687.
http://dx.doi.org/10.1074/jbc.272.12.7681

[76]. Levitski, A.; Gilan, C. Trends Pharmacol. Sci. 1991, 12, 171-174.
http://dx.doi.org/10.1016/0165-6147(91)90538-4

[77]. Groundwater, P. W.; Solomons, K. R. H.; Drewe, J. A.; Munawar, M. A. Prog. Med. Chem. 1996, 33, 233-329.
http://dx.doi.org/10.1016/S0079-6468(08)70307-2

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).