European Journal of Chemistry

Microwave assisted synthesis of 2-amino-6-methoxy-4H-benzo[h]chromene derivatives



Main Article Content

Ahmed Mohamed El-Agrody
Al-Anood Mohamed Al-Dies
Ahmed Mahmoud Fouda

Abstract

A convenient and efficient method using microwave assisted synthesis of 4H-benzo[h]chromenes (7 and 8), by the reaction of 4-methoxy-1-naphthol (1) with a mixture of aromatic aldehydes (2) and malononitrile (3) or ethyl cyanoacetate (5) and also, by the reaction of 4-methoxy-1-naphthol (1) with α-cyanocinnamonitriles (4) or ethyl α-cyanocinnamates (6) in ethanolic piperidine solution was examined. Structures of the newly synthesized compounds were established on the basis of spectral data, IR, 1H NMR, 13C NMR, 13C NMR-DEPT and MS data.


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El-Agrody, A. M.; Al-Dies, A.-A. M.; Fouda, A. M. Microwave Assisted Synthesis of 2-Amino-6-Methoxy-4H-benzo[h]chromene Derivatives. Eur. J. Chem. 2014, 5, 133-137.

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References

[1]. Kumar, D.; Buchi Reddy, V.; Sharad, S.; Dube, U.; Kapur, S. Eur. J. Med. Chem. 2009, 44, 3805-3809.
http://dx.doi.org/10.1016/j.ejmech.2009.04.017

[2]. Jeso, V.; Nicolaou, K. C. Tetrahedron Lett, 2009, 50, 1161-1163.
http://dx.doi.org/10.1016/j.tetlet.2008.12.096

[3]. Alvey, L.; Prado, S.; Saint-Joanis, B.; Michel, S.; Koch, M.; Cole, S. T.; Tillequin, F.; Janin, Y. L. Eur. J. Med. Chem. 2009, 44, 2497-2505.
http://dx.doi.org/10.1016/j.ejmech.2009.01.017

[4]. Raj, T.; Kaur, B. R.; Kumar, S. R.; Gupta, V.; Sharma, D.; Paul, S. I. M. Eur. J. Med. Chem. 2009, 44, 3209-3216.
http://dx.doi.org/10.1016/j.ejmech.2009.03.030

[5]. Kidwai, M.; Poddar, R.; Bhardwaj, S.; Singh, S.; Mehta, L. P. Eur. J. Med. Chem. 2010, 45, 5031-5038.
http://dx.doi.org/10.1016/j.ejmech.2010.08.010

[6]. DaSilva, D. B.; Tulli, E. C. O.; Militao, G. C. G.; Costa-Lotufo, L. V.; Pessoa, C.; DeMoraes, M. O.; Albuquerque S.; DeSiqueira, J. M. Phytomedicine 2009, 70, 590-595.

[7]. Tanaka, J. C. A.; Da Silva, C. C.; Ferreira, I. C. P.; Machado, G. M. C.; Leon L. L.; De Oliveira, A. J. B. Phytomedicine 2007, 14, 377-380.
http://dx.doi.org/10.1016/j.phymed.2006.09.002

[8]. Lakshmi, V.; Pandey, K.; Kapil, A.; Singh, N.; Samant M.; Dube, A. Phytomedicine 2007, 14, 36-42.
http://dx.doi.org/10.1016/j.phymed.2005.10.002

[9]. Torres-Santos, E. C.; Lopes, D.; Rodriguez, R.; Oliveira, J. P.; Carauta, P.; Bandeira Falcao, C. A.; Kaplan, M. A. C.; Rossi-Bergmann, B. Phytomedicine 2004, 11, 114-120.
http://dx.doi.org/10.1078/0944-7113-00381

[10]. Sabry, N. M.; Mohamed, H. M.; Khattab, E. S. A. E. H.; Motlaq, S. S.; El-Agrody, A. M. Eur. J. Med. Chem. 2011, 46, 765-772.
http://dx.doi.org/10.1016/j.ejmech.2010.12.015

[11]. Rampa, A.; Bisi, A.; Belluti, F.; Gobbi, S.; Piazzi, L.; Valenti, P.; Zampiron, A.; Caputo, A.; Varani, K.; Borea, P. A.; Carrara, M. Il Farmaco 2005, 60, 135-147.
http://dx.doi.org/10.1016/j.farmac.2004.09.006

[12]. Alvey, L.; Prado, S.; Huteau, V.; Saint-Joanis, B.; Michel, S.; Koch, M.; Cole, S. T.; Tillequin F.; Janin, Y. L. Bioorg. Med. Chem. 2008, 16, 8264-8272.
http://dx.doi.org/10.1016/j.bmc.2008.06.057

[13]. Symeonidis, T.; Chamilos, M.; Hadjipavlou-Litina, D. J.; Kallitsakis, M.; Litinas, K. E. Bioorg. Med. Chem. Lett. 2009, 19, 1139-1142.
http://dx.doi.org/10.1016/j.bmcl.2008.12.098

[14]. Singh, O. M.; Devi, N. S.; Thokchom, D. S.; Sharma, G. J. Eur. J. Med. Chem. 2010, 45, 2250-2257.
http://dx.doi.org/10.1016/j.ejmech.2010.01.070

[15]. Vukovic, N.; Sukdolak, S.; Solujic, S.; Niciforovic, N. Food Chem. 2010, 120, 1011-1018.
http://dx.doi.org/10.1016/j.foodchem.2009.11.040

[16]. Tandon, V. K.; Vaish, M.; Jain, S.; Bhakuni, D. S.; Srimal, R. C. Indian J. Pharm. Sci. 1991, 53, 22-27.

[17]. Magedov, I. V.; Manpadi, M.; Evdokimov, N. M.; Elias, E. M.; Rozhkova, E.; Ogasawara, M. A.; Bettale, J. D.; Przhevalskii, N. M.; Rogelj, S.; Kornienko, A. Bioorg. Med. Chem. Lett. 2007, 17, 3872-3876.
http://dx.doi.org/10.1016/j.bmcl.2007.05.004

[18]. Doshi, J. M.; Tian, D.; Xing, C. J. Med. Chem. 2006, 49, 7731-7739.
http://dx.doi.org/10.1021/jm060968r

[19]. Kessel, D.; Reiners, J. J.; Hazeldine, S. T.; Polin, L.; Horwitz, J. P. Mol. Cancer Ther. 2007, 6, 370-379.
http://dx.doi.org/10.1158/1535-7163.MCT-05-0386

[20]. Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Zhao, J.; Crogan-Grundy, C.; Xu, L.; Lamothe, S.; Gourdeau, H.; Denis, R.; Tseng, B.; Kasibhatla, S.; Cai, S. X. J. Med. Chem. 2007, 50, 2858-2864.
http://dx.doi.org/10.1021/jm070216c

[21]. Han, Q. B.; Yang, N. Y.; Tian, H. L.; Qiao, C. F.; Song, J. Z.; Chang, D. C.; Chen, S. L.; Luo, K. Q.; Xu, H. X. Phytochemistry 2008, 69, 2187-2197.
http://dx.doi.org/10.1016/j.phytochem.2008.05.019

[22]. Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Crogan-Grundy, C.; Labrecque, D.; Bubenick, M.; Attardo, G.; Denis, R.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S. X. J. Med. Chem. 2008, 51, 417-423.
http://dx.doi.org/10.1021/jm7010657

[23]. Kemnitzer, W.; Jiang, S.; Wang, Y.; Kasibhatla, S.; Crogan-Grundy, C.; Bubenick, M.; Labrecque, D.; Denis, R.; Lamothe, S.; Attardo, G.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cai, S. X. Bioorg. Med. Chem. Lett. 2008, 18, 603-607.
http://dx.doi.org/10.1016/j.bmcl.2007.11.078

[24]. Huang, W.; Ding, Y.; Miao, Y.; Liu, M. Z.; Li, Y.; Yang, G. F. Eur. J. Med. Chem. 2009, 44, 3687-3696.
http://dx.doi.org/10.1016/j.ejmech.2009.04.004

[25]. Mahmoodi, M.; Aliabadi, A.; Emami, S.; Safavi, M.; Rajabalian, S.; Mohagheghi, M. A.; Khoshzaban, A.; Samzadeh-Kermani, A.; Lamei, N.; Shafiee, A.; Foroumadi, A. Arch. Pharm. Chem. 2010, 343, 411-416.
http://dx.doi.org/10.1002/ardp.200900198

[26]. Endo, S.; Matsunaga, T.; Kuwata, K.; Zhao, H. T.; El-Kabbani, O.; Kitade, Y.; Hara, A. Bioorg. Med. Chem. 2010, 18, 2485-2490.
http://dx.doi.org/10.1016/j.bmc.2010.02.050

[27]. Tseng, T. H.; Chuang, S. K.; Hu, C. C.; Chang, C. F.; Huang, Y. C.; Lin, C. W.; Lee, Y. J. Tetrahedron 2010, 66, 1335-1340.
http://dx.doi.org/10.1016/j.tet.2009.12.002

[28]. Bruhlmann, C.; Ooms, F.; Carrupt, P.; Testa, B.; Catto, M.; Leonetti, F.; Altomare, C.; Cartti, A. J. Med. Chem. 2001, 44, 3195-3198.
http://dx.doi.org/10.1021/jm010894d

[29]. Kesten, S. R.; Heffner, T. G.; Johnson, S. J.; Pugsley, T. A.; Wright, J. L.; Wise, D. L. J. Med. Chem. 1999, 42, 3718-3725.
http://dx.doi.org/10.1021/jm990266k

[30]. Lee, K. S.; Khil, L. Y.; Chae, S. H.; Kim, D.; Lee, B. H.; Hwang, G. S.; Moon, C. H.; Chang, T. S.; Moon, C. K. Life Sci. 2006, 78, 1091-1097.
http://dx.doi.org/10.1016/j.lfs.2005.06.017

[31]. Coudert, P.; Coyquelet, J. M.; Bastide, J.; Marion Y.; Fialip, J. Ann. Pharm. Fr. 1988, 46, 91-96.

[32]. Gajbhiye, A.; Mallareddy, V.; Achaiah, G. Indian J. Pharm. Sci. 2008, 70, 118-120.
http://dx.doi.org/10.4103/0250-474X.44589

[33]. Ghate, M.; Kusanur, R. A.; Kulkarni, M. V. Eur. J. Med. Chem. 2005, 40, 882-887.
http://dx.doi.org/10.1016/j.ejmech.2005.03.025

[34]. El-Sayed, A. T.; Ibrahim, M. A. J. Braz. Chem. 2010, 21, 1007-1016.
http://dx.doi.org/10.1590/S0103-50532010000600010

[35]. Amin, K. M.; Kamel, M. M.; Anwar, M. M.; Khedr M.; Syam, Y. M. Eur. J. Med. Chem. 2010, 45, 2117-2131.
http://dx.doi.org/10.1016/j.ejmech.2009.12.078

[36]. Keri, R. S.; Hosamani, K. M.; Shingalapur, R. V.; Hugar, M. H. Eur. J. Med. Chem. 2010, 45, 2597-2605.
http://dx.doi.org/10.1016/j.ejmech.2010.02.048

[37]. Sashidhara, K. V.; Kumar, M.; Modukuri, R. K.; Srivastava, A.; Puri, A. Bioorg. Med. Chem. Lett. 2011, 21, 6709-6713.
http://dx.doi.org/10.1016/j.bmcl.2011.09.053

[38]. Hiramoto, K.; Nasuhara, A.; Michiloshi, K.; Kato, T.; Kikugawa, K. Mutation Res. 1997, 395, 47-56.
http://dx.doi.org/10.1016/S1383-5718(97)00141-1

[39]. Yavari, I.; Djahaniani, H.; Nasiri, F. Synthesis 2004, 679-682.
http://dx.doi.org/10.1055/s-2004-815990

[40]. Yavari, I.; Djahaniani, H.; Nasiri, F. Tetrahedron 2003, 59, 9409-9412.
http://dx.doi.org/10.1016/j.tet.2003.09.072

[41]. Gong, K.; Wang, H. L.; Fang, D.; Liu, Z. L. Catal. Commun. 2008, 9, 650-563.
http://dx.doi.org/10.1016/j.catcom.2007.07.010

[42]. Abd-El-Aziz, A. S.; El-Agrody, A. M.; Bedair, A. H.; Corkery, T. C.; Ata, A. Heterocycles 2004, 63, 1793-1312.
http://dx.doi.org/10.3987/COM-04-10089

[43]. Kemnitzer, W.; Kasibhatla, S.; Jiang, S.; Zhang, H.; Zhao, J.; Lia, S.; Xu, L.; Crogan-Grundy, C.; Denis, R.; Barriault, N.; Villacourt, L.; Charron, S.; Dodd, J.; Attardo, G.; Labrique, D.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cia, S. X. Bioorg. Med. Chem. Lett. 2005, 15, 4745-4751.
http://dx.doi.org/10.1016/j.bmcl.2005.07.066

[44]. Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Wang, W.; Lia, S.; Xu, L.; Crogan-Grundy, C.; Denis, R.; Barriault, N.; Villacourt, L.; Charron, S.; Dodd, J.; Attardo, G.; Labrique, D.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Drewe, J.; Cia, S. X. J. Med. Chem. 2004, 47, 6299-6310.
http://dx.doi.org/10.1021/jm049640t

[45]. Dyachenko, V. D.; Chernega, A. N. Russ. J. Org. Chem. 2006, 42, 567-576.
http://dx.doi.org/10.1134/S1070428006040142

[46]. Ballini, R.; Bosica, G.; Conforti, M. L.; Maggi, R.; Mazzacanni, A.; Righi, P.; Sartori, G. Tetrahedron 2001, 57, 1395-1398.
http://dx.doi.org/10.1016/S0040-4020(00)01121-2

[47]. Jin, T. S.; Xiao, J. C.; Wang S. J.; Li, T. S. Ultrson. Sonochem. 2004, 11, 393-397.

[48]. Du, Z.; Siau, W. Y.; Wang, J. Tetrahedron Lett. 2011, 52, 6137-6141.
http://dx.doi.org/10.1016/j.tetlet.2011.09.030

[49]. Radomkit, S.; Sarnpitak, P.; Tummatorn, J.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. Tetrahedron 2011, 67, 3904-3914.
http://dx.doi.org/10.1016/j.tet.2011.03.059

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

[51]. Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
http://dx.doi.org/10.1002/anie.200400655

[52]. Bose, A. K.; Manhas, M. S.; Ganguly, S. N.; Sharma, A. H.; Banik, B. K. Synthesis 2002, 1578-1591.
http://dx.doi.org/10.1055/s-2002-33344

[53]. Varma, R. S. Green Chem. 1999, 1, 43-55.
http://dx.doi.org/10.1039/a808223e

[54]. Shi, L.; Wang, M.; Fan, C. A.; Zhang, F. M.; Tu, Y. Q. Org. Lett. 2003, 5, 3515-3517.
http://dx.doi.org/10.1021/ol0353868

[55]. Shi, L.; Wang, M.; Fan, C. A.; Zhang, F. M.; Tu, Y. Q. Org. Lett. 2004, 6, 1001-1003.
http://dx.doi.org/10.1021/ol049936t

[56]. Wu, X.; Larhed, M. Org. Lett. 2005, 7, 3327-3329.
http://dx.doi.org/10.1021/ol0512031

[57]. Hamelin, J.; Bazureau, J. P.; Texier-Boullet, F., In Microwaves in Organic Synthesis, Ed.: Loupy, A., Wiley-VCH, Weinheim, Germany, 2002, pp. 253.
http://dx.doi.org/10.1002/3527601775.ch8

[58]. Kidwai, M.; Saxena, S.; Khan, M. K. R.; Thukra, S. S. Bioorg. Med. Chem. Lett. 2005, 15, 4295-4298.
http://dx.doi.org/10.1016/j.bmcl.2005.06.041

[59]. Surpur, M. P.; Kshirsagar, S.; Samant, S. D. Tetrahedron Lett. 2009, 50, 719-722.
http://dx.doi.org/10.1016/j.tetlet.2008.11.114

[60]. Mekheimer, R. A.; Sadek, K. U. Chin. Chem. Lett. 2009, 271-274.
http://dx.doi.org/10.1016/j.cclet.2008.11.025

[61]. El-Agrody, A. M. J. Chem. Res. (S) 1994, 280-281.

[62]. 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.

[63]. El-Agrody, A. M.; Emam, H. A.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H. J. Chem. Res. (M) 1997, 2039-2048.

[64]. Bedair, A. H.; El-Hady, N. A.; Abd El-Latif, M. S.; Fakery, A. H.; El-Agrody, A. M. Il Farmaco 2000, 55, 708-714.
http://dx.doi.org/10.1016/S0014-827X(00)00097-5

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

[66]. Sayed, A. Z.; El-Hady, N. A.; El-Agrody, A. M. J. Chem. Res. (S) 2000, 164-166.

[67]. El-Agrody, A. M.; Abd El-Latif, M. S.; El-Hady, N. A.; Fakery, A. H.; Bedair, A. H. Molecules 2000, 6, 519-527.
http://dx.doi.org/10.3390/60600519

[68]. Bedair, A. H.; Emam, H. A.; El-Hady, N. A.; Ahmed, K. A. R.; El-Agrody, A. M. Il Farmaco 2001, 56, 965-973.
http://dx.doi.org/10.1016/S0014-827X(01)01168-5

[69]. El-Agrody, A. M.; Eid, F. A.; Emam, H. A.; Mohamed, H. M.; Bedair, A. H. Z. Naturforsch. Teil B 2002, 57, 579-585.

[70]. Khafagy, M. M.; Abd El-Wahab, A. H. F.; Eid, F. A.; El-Agrody, A. M. Il Farmaco 2002, 57, 715-722.
http://dx.doi.org/10.1016/S0014-827X(02)01263-6

[71]. Eid, F. A.; Bedair, A. H.; Emam, H. A.; Mohamed, H. M.; El-Agrody, A. M. Al-Azhar Bull. Sci. 2003, 14, 311-342.

[72]. Abd-El-Aziz, A. S.; Mohamed, H. M.; Mohammed, S.; Zahid, S.; Ata, A.; Bedair, A. H.; El-Agrody, A. M.; Harvey, P. D. J. Heterocycl. Chem. 2007, 44, 1287-1300.
http://dx.doi.org/10.1002/jhet.5570440610

[73]. El-Agrody, A. M.; Sabry, N. M.; Motlaq, S. S. J. Chem. Res. 2011, 35, 77-83.
http://dx.doi.org/10.3184/174751911X12964930076728

[74]. Al-Dies, Al-Anood M.; Amr, Abdel-Galil E.; El-Agrody, A. M.; Chia, Tze Shyang; Fun, Hoong-Kun Acta Cryst. E 2012, 68, 1934-1935.

[75]. Al-Sehemi, A. G.; Irfan, A.; El-Agrody, A. M. J. Mol. Struct. 2012, 1018, 171-175.
http://dx.doi.org/10.1016/j.molstruc.2012.03.018

[76]. El-Agrody, A. M.; Mohamed, A. A.; Amr, A. E.; Tze, S.; Fun, H. K. Acta Cryst. E 2012, 68, 1803-1804.
http://dx.doi.org/10.1107/S1600536812021939

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