European Journal of Chemistry

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

Article Sidebar

PDF
Published: Jun 30, 2016
DOI: https://doi.org/10.5155/eurjchem.7.2.230-237.1432
Keywords:
Naphthopyran, α-Cyanocinnamonitriles, Ethyl α-cyanocinnamates, Naphthopyranopyrimidines, 4-Phenyldiazenyl-1-naphthol, 4-(p-Tolyldiazenyl)-1-naphthol
Section
Research Article
Issue
Vol. 7 No. 2 (2016): June 2016
Dates
Received 2016-03-27
Accepted 2016-04-29
Published 2016-06-30


Main Article Content

Ibrahim Ali Radini
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
Ashraf Hassan Fekry Abd El-Wahab
Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia

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.


icon graph This Abstract was viewed 1927 times | icon graph Article PDF downloaded 894 times

How to Cite
(1)
Radini, I. A.; Abd El-Wahab, A. H. F. Heteroaromatization With 4-Phenyldiazenyl-1-Naphthol. Part I: Synthesis of Some New Naphthopyrans and Naphthopyranopyrimidines. Eur. J. Chem. 2016, 7, 230-237.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
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

Supporting Agencies

Chemistry Department, Faculty of Science, Jazan University, 2097, Jazan, Kingdom of Saudi Arabia
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 © 2025 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).