European Journal of Chemistry 2016, 7(2), 230-237 | doi: https://doi.org/10.5155/eurjchem.7.2.230-237.1432 | Get rights and content

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Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines


Ibrahim Ali Radini (1) , Ashraf Hassan Fekry Abd El-Wahab (2,*)

(1) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(2) Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 27 Mar 2016 | Revised: 27 Apr 2016 | Accepted: 29 Apr 2016 | Published: 30 Jun 2016 | Issue Date: June 2016

Abstract


Reaction of 4-phenyldiazenyl /or 4-(p-tolyldiazenyl)-1-naphthol (1) with various substituted α-cyanocinnamonitriles (2a-h) and ethyl α-cyanocinnamates (2i-p) afforded 2-amino-4-(aryl)-6-(phenyldiazenyl /or p-tolyldiazenyl)-4H-naphtho[1,2-b]pyrano-3-carbonitrile (3a-h) and ethyl 2-amino-4-(aryl)-6-(phenyldiazenyl /or p-tolyldiazenyl)-4H-naphtho[1,2-b]pyrano-3-carboxylate (3i-p). Reaction of compound 3a with Ac2O or PhCOCl and formic acid afforded N-acetylamino or N,N-dibenzoylamino and naphthopyranopyrimidine derivatives (4-8), respectively. The structures of these compounds were established on the basis of IR, UV, 1H NMR, 13C NMR, and MS data.


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Keywords


Naphthopyran; α-Cyanocinnamonitriles; Ethyl α-cyanocinnamates; Naphthopyranopyrimidines; 4-Phenyldiazenyl-1-naphthol; 4-(p-Tolyldiazenyl)-1-naphthol

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DOI: 10.5155/eurjchem.7.2.230-237.1432

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Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia

Citations

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[2]. Hany M. Mohamed, Ashraf H.F. Abd El-Wahab
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[3]. Hany Mostafa Mohamed, Ashraf Hassan Fekry Abd El-Wahab, Tarek Maamon El-Gogary
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[4]. Ashraf HF Abd El-Wahab, Ahmed H Bedair, Fawzy M Ali A, Ahmed HA Halawa, Ahmed M El-Agrody
Synthesis, reactions, of naphtho[2,1-b]furan derivatives and antimicrobial activity
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[5]. Ibrahim Ali Radini, Hany Mostafa Hamed, Mohammed Abdo Yahya Kharir, Ashraf Hassan Fekry Abd Elwahab
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References


[1]. Wojciechowski, K.; Wyrebak, A.; Gumulak, J. Dyes Pigments 2003, 56, 99-106.
http://dx.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.
http://dx.doi.org/10.1016/S0223-5234(03)00081-3

[3]. Mittal, A.; Kurup, L.; Mittal, J. J. Hazard. Mater. 2007, 146, 243-248.
http://dx.doi.org/10.1016/j.jhazmat.2006.12.012

[4]. Wainwright, M. Dyes Pigments 2008, 76, 582-589.
http://dx.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.
http://dx.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.
http://dx.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.
http://dx.doi.org/10.1039/b406228k

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

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

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

[14]. Browing, C. H.; Cohen, J. B.; Ellingworth, S.; Gulbransen, R. Journal Storage 1926, 100, 293-325.

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

[16]. Pagga, U.; Brown, D. Chemosphere 1986, 15, 479-491.
http://dx.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.
http://dx.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, Farmaco 2000, 55, 708-714.
http://dx.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.
http://dx.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.
http://dx.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.
http://dx.doi.org/10.1021/jm9703754

[24]. 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

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

[26]. Dell, C. P.; Smith, C. W. European Patent Appl. 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.
http://dx.doi.org/10.2174/157018012800389331

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

[31]. 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

[32]. 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.
http://dx.doi.org/10.1039/a608348j

[33]. 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.

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

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

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

[37]. Abd-El-Aziz, A. S; El-Agrody, A. M.; Bedair, A. H.; Christopher, C. T.; Ata, A. Heterocycles 2004, 63, 1793-1812.
http://dx.doi.org/10.3987/COM-04-10089

[38]. Dave, K. G.; Shishoo, C. J.; Devani, M. B.; Kalyanaraman, R.; Ananthan, S.; Ullas, G. V.; Bahadit, V. S. J. Heterocycl. Chem. 1980, 1497-1501.
http://dx.doi.org/10.1002/jhet.5570170727


How to cite


Radini, I.; Abd El-Wahab, A. Eur. J. Chem. 2016, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432
Radini, I.; Abd El-Wahab, A. Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines. Eur. J. Chem. 2016, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432
Radini, I., & Abd El-Wahab, A. (2016). Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines. European Journal of Chemistry, 7(2), 230-237. doi:10.5155/eurjchem.7.2.230-237.1432
Radini, Ibrahim, & Ashraf Hassan Fekry Abd El-Wahab. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines." European Journal of Chemistry [Online], 7.2 (2016): 230-237. Web. 4 Jun. 2023
Radini, Ibrahim, AND Abd El-Wahab, Ashraf. "Heteroaromatization with 4-phenyldiazenyl-1-naphthol. Part I: Synthesis of some new naphthopyrans and naphthopyranopyrimidines" European Journal of Chemistry [Online], Volume 7 Number 2 (30 June 2016)

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