European Journal of Chemistry 2017, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632

Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives


Hany Mostafa Mohamed (1) , Ashraf Hassan Fekry Abd El-Wahab (2,*) , Tarek Maamon El-Gogary (3)

(1) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom Saudi Arabia
(2) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom Saudi Arabia
(3) Chemistry Department, Faculty of Science (Domyat), Damietta University, 34517, Domyat Al-Gideda, Egypt
(*) Corresponding Author

Received: 21 Jul 2017, Accepted: 04 Sep 2017, Published: 31 Dec 2017

Abstract


A one pot three component reaction of 4-phenyldiazenyl-1-naphthol (1), p-chloro benzaldehyde (2) and malononitrile or ethyl cyanoacetate (3) in ethanol/piperidine under reflux afforded 2-amino-4-(p-chlorophenyl)-6-phenyldiazenyl-4H-naphtho[1,2-b]pyrano-3-carbonitrile (4a) and ethyl 2-amino-4-(p-chlorophenyl)-6-phenyldiazenyl-4H-naphtho[1,2-b]pyrano -3-carboxylate (4b). Structure of these compounds was established on the basis of IR, 1H NMR, 13C NMR, Mass and UV-Vis spectra. Molecular geometry of compounds 4a and b was obtained at B3LYP/6-31+G(d) level. Two tautomers and two conformers were geometrically optimized. The tautomers are separated by about 7.942 kcal/mol while rotational conformers are only separated by 0.511 kcal/mol. Molecular reactivity descriptors including global electrophilicity, hardness, softness and local condensed Fukui functions were computed and discussed. Frontier molecular orbitals (HOMO and LUMO) were also computed.


Keywords


Malononitrile; Fukui functions; Ethyl cyanoacetate; 4-Phenyldiazenyl-1-naphthol; 4H-Naphthopyran derivatives; Density Functional Theory (DFT)

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.8.4.358-366.1632

Get Citation | Scilit | GrowKudos | ResearchGate | Publons | Microsoft Academic

WorldCat | Dimensions | SemanticScholar | PlumX Metrics | Kopernio | Zotero | Mendeley

Article Metrics


This Abstract was viewed 593 times | PDF Article downloaded 201 times


References

[1]. Wojciechowski, K.; Wyrebak, A.; Gumulak, J. Dyes Pigments 2003, 56, 99-106.
https://doi.org/10.1016/S0143-7208(02)00130-4

[2]. Rudyk, H.; Knaggs, M. H.; Vasiljevic, S.; Hope, J.; Birkett, C.; Gilbert, I. H. Eur. J. Med. Chem. 2003, 38, 567-579.
https://doi.org/10.1016/S0223-5234(03)00081-3

[3]. Mittal, A.; Kurup, L.; Mittal, J. J. Hazard. Mater. 2007, 142, 243-248.
https://doi.org/10.1016/j.jhazmat.2006.12.012

[4]. Wainwright, M. Dyes Pigments 2008, 76, 582-589.
https://doi.org/10.1016/j.dyepig.2007.01.015

[5]. Ahmed, A. E. I.; Hay, J. N.; Bushell, M. E; Wardell, J. N.; Cavalli, G. React. Funct. Polym. 2008, 68, 248-260.
https://doi.org/10.1016/j.reactfunctpolym.2007.09.004

[6]. Simu, G.; Chicu, S. A.; Morin, N.; Schmidt, W.; Sisu, E. Turk. J. Chem. 2004, 28, 579-585.

[7]. Simu, G. M.; Hora, S. G.; Grad, M. E; Sisu, E. N. V. Rev. Roum. Chim. 2005, 50, 113-117.

[8]. Bae, J. S.; Freeman, H. S.; El-Shafei, A. Dyes Pigments 2003, 57, 121-129.
https://doi.org/10.1016/S0143-7208(02)00120-1

[9]. Combellas, C.; Kanoufi, F.; Pinson, H.; Podyorica, F. Am. Chem. Soc. 2008, 34, 429-436.

[10]. Pinson, J.; Podyorica, F. Chem. Soc. Rev. 2005, 34, 429-444.
https://doi.org/10.1039/b406228k

[11]. Dabbagh, H. A.; Teimouri, A.; Chermahini, A. N. Dyes Pigments 2007, 73, 239-244.
https://doi.org/10.1016/j.dyepig.2005.12.002

[12]. Murray, P. S.; Ralph, S. F. Electrochimica Acta 2006, 51, 2471-2476.
https://doi.org/10.1016/j.electacta.2005.07.029

[13]. Garg, H. G.; Praksh, C. J. Med. Chem. 1972, 15, 435-436.
https://doi.org/10.1021/jm00274a035

[14]. Browing, C. H.; Cohen, J. B.; Ellingworth, S.; Gulbransen, R. Journal Storage 1926, 100, 293-25.

[15]. Khalid, A.; Arshad, M.; Crowley, D. E. Appl. Microbiol. Biotech. 2008, 78, 361-369.
https://doi.org/10.1007/s00253-007-1302-4

[16]. Pagga, U.; Brown, D. Chemosphere. 1986, 15, 479-491.
https://doi.org/10.1016/0045-6535(86)90542-4

[17]. Farghaly, T. A.; Abdallah, Z. A. Arkivoc 2008, 17, 295-305.

[18]. El-Agrody, A. M.; Abd El-Latif, M. S.; El-Hady, N. A.; Fakery, A. H.; Bedair, A. H. Molecules 2001, 6, 519-527.
https://doi.org/10.3390/60600519

[19]. 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.
https://doi.org/10.1016/S0014-827X(00)00097-5

[20]. 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.

[21]. Abd El-Wahab A. H. F. Pharmaceuticals 2012, 5, 745-757.
https://doi.org/10.3390/ph5070745

[22]. Smith, W. P.; Sollis, L. S.; Howes, D. P.; Cherry, C. P.; Starkey, D. I.; Cobley, N. K. J. Med. Chem. 1998, 41, 787-797.
https://doi.org/10.1021/jm970374b

[23]. Taylor, R. N,; Cleasby, A.; Singh, O.; Sharzynski, T.; Wonacott, J. A.; Smith, W. P.; Sollis, L. S.; Howes, D. P.; Cherry, C. P.; Bethell, R.; Colman, P.; Varghese, J. J. Med. Chem. 1998, 41, 798-807.
https://doi.org/10.1021/jm9703754

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

[25]. Martinez, A. G.; Marco, L. J. Bioorg. Med. Chem. Lett. 1997, 7, 3165-3170.
https://doi.org/10.1016/S0960-894X(97)10165-2

[26]. Dell, C. P.; Smith, C. W., European Patent Applications EP 537949, Chem. Abstr. 1993, 119, 139102d.

[27]. Bianchi, G.; Tava, A. Agric. Biol. Chem. 1987, 51, 2001-2002.

[28]. Mohr, S. J.; Chirigos, M. A.; Fuhrman, F. S.; Pryor, J. W. Cancer Res. 1975, 35, 3750-3754.

[29]. Al-Ghamdi, A. M.; Abd EL-Wahab, A. H. F.; Mohamed, H. M.; El-Agrody, M. A. Lett. Drug Des. Discov. 2012, 9, 459-470.

[30]. Eiden, F.; Denk, F. Arch. Pharm. Weinheim Ger. (Arch. Pharm.) 1991, 324, 353-354.
https://doi.org/10.1002/ardp.19913240606

[31]. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; P. Hratchian, H.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al‐Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. et al., Gaussian 09, revision A. 02, Gaussian, Inc., Wallingford CT, 2009.

[32]. Delley B. J. Chem. Phys. 1990, 92(1), 508-517.
https://doi.org/10.1063/1.458452

[33]. Delley B. J. Chem. Phys. 2000, 113(18), 7756-7764.
https://doi.org/10.1063/1.1316015

[34]. Accelrys Software Inc., Material Studio Modeling Environment, Release v7. 0, San Diego: Accelrys Software Inc., 2013.

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

[36]. El-Agrody, A. M.; Emam, H. A.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H. J. Chem. Res. (S) 1997, 9, 320-321.
https://doi.org/10.1039/a608348j

[37]. El-Agrody, A. M.; Emam, H. A.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H. J. Chem. Res. (M) 1997, 9, 2039-2048.

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

[39]. Ashraf, H. F. A.; Hany, M. M.; Ahmed, M. E.; Ahmed, H. B. Eur. J. Chem. 2013, 4(4), 467-483.
https://doi.org/10.5155/eurjchem.4.4.467-483.775

[40]. Radini, I. A.; El-Wahab, A. H. F. A. Eur. J. Chem. 2010, 7(2), 230-237.
https://doi.org/10.5155/eurjchem.7.2.230-237.1432

[41]. Wolinsky, J.; Hauer, H. S. J. Org. Chem. 1969, 34, 3169-3170.
https://doi.org/10.1021/jo01262a077

[42]. Parthasarathi, R.; Padmanabhan, J.; Subramanian, V.; Maiti, B.; Chattaraj, P. K. J. Phys. Chem. A 2003, 107(48), 10346-10352.
https://doi.org/10.1021/jp035620b

[43]. Fukui, K.; Yonezaw, T.; Shingu, H. J. Chem. Phys. 1952, 20, 722-725.
https://doi.org/10.1063/1.1700523

[44]. Parr, R. G.; Yang, W. J. Am. Chem. Soc. 1984, 106, 4049-4050.
https://doi.org/10.1021/ja00326a036

[45]. Yang, W.; Parr, R. G. Natl. Acad. Sci. U. S. A. 1985, 82, 6723-6726.
https://doi.org/10.1073/pnas.82.20.6723

[46]. Gunasekaran, S.; Balaji, R. A.; Kumeresan, S.; Anand, G.; Srinivasan, S. Can. J. Anal. Sci. Spectrosc. 2008, 53, 149-162.

[47]. Durig, J. R.; Little, T. S.; Gounev, T. K.; Gardner, J. K.; Sullivan, J. F. Mol. Struct. 1996, 375(1), 83-94.

[48]. Kosar, B.; Albayrak, C. Spectrochim. Acta. A 2011, 78(1), 160-167.
https://doi.org/10.1016/j.saa.2010.09.016

[49]. Sajan, D.; Lakshmi, K. U.; Erdogdu, Y.; Joe, I. H. Spectrochim. Acta. A 2011, 78(1), 113-121.
https://doi.org/10.1016/j.saa.2010.09.007


How to cite


Mohamed, H.; Abd El-Wahab, A.; El-Gogary, T. Eur. J. Chem. 2017, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632
Mohamed, H.; Abd El-Wahab, A.; El-Gogary, T. Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives. Eur. J. Chem. 2017, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632
Mohamed, H., Abd El-Wahab, A., & El-Gogary, T. (2017). Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives. European Journal of Chemistry, 8(4), 358-366. doi:10.5155/eurjchem.8.4.358-366.1632
Mohamed, Hany, Ashraf Hassan Fekry Abd El-Wahab, & Tarek Maamon El-Gogary. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives." European Journal of Chemistry [Online], 8.4 (2017): 358-366. Web. 7 Dec. 2019
Mohamed, Hany, Abd El-Wahab, Ashraf, AND El-Gogary, Tarek. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part III: One-pot synthesis and DFT study of 4H-naphthopyran derivatives" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

DOI Link: https://doi.org/10.5155/eurjchem.8.4.358-366.1632

| | | | |

| | | | | |

.

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.