Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination
Amr Mohamed Abdelmoniem (1,*)
, Said Ahmed Soliman Ghozlan (2) , Holger Butenschön (3) , Ismail Abdelshafy Abdelhamid (4) (1) Department of Chemistry, Faculty of Science, Cairo University, 12613 Giza, Egypt
(2) Department of Chemistry, Faculty of Science, Cairo University, 12613 Giza, Egypt
(3) Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany
(4) Department of Chemistry, Faculty of Science, Cairo University, 12613 Giza, Egypt
(*) Corresponding Author
Received: 23 Nov 2015 | Revised: 12 Dec 2015 | Accepted: 19 Dec 2015 | Published: 31 Mar 2016 | Issue Date: March 2016
Abstract
Michael addition reactions of arylhydrazone derivatives with different functionalized α-cyanoacrylamides were conducted and yielded new pyridazine-4-carboxamide compounds. A further reaction with acetic anhydride was investigated resulting in the formation of a 4-deazatoxoflavin analogue. A one step synthesis of 4-deazatoxoflavin was also carried out by reacting azaenamine with N-carbamoyl-2-cyano-3-phenylacrylamide to give deazatoxoflavin. Unambiguous structural elucidation was done using 2D-HMBC spectroscopy.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.7.1.73-80.1371
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 1474 times |
PDF Article downloaded 659 times
Funding information
The Alexander von Humboldt foundation (AvH), Germany
Citations
[1]. Fatma M. Saleh, Hamdi M. Hassaneen, Amr M. Abdelmoniem, Ahmed H. M. Elwahy, Ismail A. Abdelhamid
Synthesis of Novel Bis(pyrido[2,1‐a]isoquinolines) Linked to Aliphatic or Aromatic Core via Ether Linkage
Journal of Heterocyclic Chemistry 56(7), 1914, 2019
DOI: 10.1002/jhet.3565
[2]. Amr M. Abdelmoniem, Mohamed Gamal Mohamed Abdelrahman, Said Ahmed Soliman Ghozlan, Ismail A. Abdelhamid
Synthesis of novel hexahydroquinolines and 6‐amino‐2‐oxopyridine‐3,5‐dicarbonitriles incorporating sulfamethoxazole via [3 + 3] annulation
Journal of Heterocyclic Chemistry 56(12), 3387, 2019
DOI: 10.1002/jhet.3737
[3]. Said A.S. Ghozlan, Doaa M. Abdelmoniem, Hamdi M. Hassaneen, Amr M. Abdelmoniem, Ismail A. Abdelhamid
Cyclic Enaminone Incorporating 5‐cyanomethylpyrazole‐4‐carbonitrile: Unexpected Formation of Pyrazolo[l,5‐a]pyridine Derivatives
Journal of Heterocyclic Chemistry 55(7), 1798, 2018
DOI: 10.1002/jhet.3220
[4]. Amr M. Abdelmoniem, Said A. S. Ghozlan, Doaa M. Abdelmoniem, Ahmed H. M. Elwahy, Ismail A. Abdelhamid
3‐Amino‐5‐cyanomethylpyrazole‐4‐carbonitrile: Versatile Reagent for Novel Bis(pyrazolo[1,5‐a]pyridine) Derivatives via a Multicomponent Reaction
Journal of Heterocyclic Chemistry 55(12), 2792, 2018
DOI: 10.1002/jhet.3346
References
[1]. Zeid, I. F.; Said, M. M.; Darwish, S. A.; Soliman, F. M. Monatsh. Chem. 2014, 145, 639-650.
http://dx.doi.org/10.1007/s00706-013-1124-2
[2]. Tucaliuc, R. A.; Cotea, V. V.; Niculaua, M.; Tuchilus, C.; Mantu, D.; Mangalagiu, I. I. Eur. J. Med. Chem. 2013, 67, 367-372.
http://dx.doi.org/10.1016/j.ejmech.2013.04.069
[3]. Deeb, A. A.; El‐Eraky, W. I.; Mohamed, S. M. Eur. J. Chem. 2015, 6(1), 88‐92.
http://dx.doi.org/10.5155/eurjchem.6.1.88-92.1166
[4]. Budhlakoti, P.; Kumar, Y.; Verma, A.; Alok, S. Int. J. Pharm. Sci. Res. 2013, 4, 1524-1528.
[5]. Elnagdi, M. H.; Al-Awadi, N. A.; Abdelhamid, I. A. Adv. Heterocycl. Chem. 2009, 79, 1-43.
http://dx.doi.org/10.1016/S0065-2725(08)00201-8
[6]. Baird, M. S.; Hussain, H. H. Tetrahedron 1987, 43, 215-224.
http://dx.doi.org/10.1016/S0040-4020(01)89947-6
[7]. Heydt, H.; Busch, K. H.; Regitz, M. Liebigs Ann. Chem. 1980, 1980, 590-599.
[8]. Heydt, H.; Breiner, H. W.; Hell, V.; Regitz, M. Z. Naturforsch. B: Chem. Sci. 1987, 42, 210-216.
http://dx.doi.org/10.1515/znb-1987-0215
[9]. Regitz, M.; Welter, W.; Hartmann, A. Chem. Ber. 1979, 112, 2509-2527.
http://dx.doi.org/10.1002/cber.19791120720
[10]. Boitsov, V. M.; Kostikov, R. R.; Molchanov, A. P.; Stepakov, A. V.; Baird, M. S. Russ. J. Org. Chem. 2004, 40, 1760-1763.
http://dx.doi.org/10.1007/s11178-005-0095-0
[11]. Groselj, U.; Meden, A.; Stanovnik, B.; Svete, J. Tetrahedron Asymm. 2007, 18, 2746-2757.
http://dx.doi.org/10.1016/j.tetasy.2007.11.012
[12]. Han, J. L.; Ong, C. W. Tetrahedron 2006, 62, 8169-8172.
http://dx.doi.org/10.1016/j.tet.2006.05.082
[13]. Ursic, U.; Groselj, U.; Meden, A.; Svete, J.; Stanovnik, B. Synthesis 2009, 2009, 217-226.
[14]. Devaraj, N. K.; Weissleder, R.; Hilderbrand, S. A. Bioconjugate chem. 2008, 19, 2297-2299.
[15]. Liu, D. S.; Tangpeerachaikul, A.; Selvaraj, R.; Taylor, M. T.; Fox, J. M.; Ting, A. Y. J. Am. Chem. Soc. 2012, 134, 792-795.
http://dx.doi.org/10.1021/ja209325n
[16]. Yang, J.; Seckute, J.; Cole, C. M.; Devaraj, N. K. Angew. Chem., Int. Ed. 2012, 51, 7476-7479.
http://dx.doi.org/10.1002/anie.201202122
[17]. Ghozlan, S. A. S.; Abdelhamid, I. A.; Elnagdi, M. H. Arkivoc 2006, 13, 147-153.
[18]. Ghozlan, S. A. S.; Abdelhamid, I. A.; Hassaneen, H. M.; Elnagdi, M. H. J. Heterocycl. Chem. 2007, 44, 105-108.
http://dx.doi.org/10.1002/jhet.5570440118
[19]. Abdelhamid, I. A. Synlett 2009, 2009(4), 625-627.
http://dx.doi.org/10.1055/s-0028-1087558
[20]. Abdelhamid, I. A.; Mohamed, M. H.; Abdelmoniem, A. M.; Ghozlan, S. A. S. Tetrahedron 2009, 65, 10069-10073.
http://dx.doi.org/10.1016/j.tet.2009.09.081
[21]. Abdelhamid, I. A.; Darwish, E. S.; Nasra, M. A.; Abdel-Gallil, F. M.; Fleita, D. H. Synthesis 2010, 2010, 1107-1112.
[22]. Ghozlan, S. A. S.; Abdelmoniem, A. M.; Abdelhamid, I. A. Curr. Org. Chem. 2011, 15, 3098-3119.
http://dx.doi.org/10.2174/138527211798357137
[23]. Brehme, R.; Enders, D.; Fernandez, R.; Lassaletta, J. M. Eur. J. Org. Chem. 2007, 2007, 5629-5660.
[24]. Reynolds, G. A.; VanAllan, J. A. Org. Synth. 1952, 32, 84-86.
http://dx.doi.org/10.15227/orgsyn.032.0084
[25]. Jones, G. Org. React. 1967, 15, 204-599.
[26]. Chen, Y.; Barber, J. R.; Ng, S. C.; Zhou, Y., Synth. Commun. 2010, 40, 821-832.
http://dx.doi.org/10.1080/00397910903013788
[27]. Turbiak, A. J.; Kampf, J. W.; Hollis Showalter, H. D. Tetrahedron Lett. 2010, 51, 1326-1328.
http://dx.doi.org/10.1016/j.tetlet.2010.01.007
[28]. El Rady, E. A.; Barsy, M. A. J. Heterocycl. Chem. 2006, 43, 243-248.
http://dx.doi.org/10.1002/jhet.5570430201
[29]. Yoneda, F.; Nakagawa, K.; Noguchi, M.; Higuchi, M. Chem. Pharm. Bull. 1981, 29, 379-385.
http://dx.doi.org/10.1248/cpb.29.379
[30]. Billings, B. K.; Wagner, J. A.; Cook, P. D.; Castle, R. N. J. Heterocycl. Chem. 1975, 12, 1221-1224.
http://dx.doi.org/10.1002/jhet.5570120625
[31]. Latuasan, H. E.; Berends, W. Biochim. Biophys. Acta 1954, 52, 502-508.
http://dx.doi.org/10.1016/0006-3002(61)90408-5
[32]. Naya, S.; Shibayama, K.; Nitta, M. Heterocycles 2004, 63, 1393-1408.
http://dx.doi.org/10.3987/COM-04-10063
[33]. Yoneda, F.; Nakagawa, K.; Koshiro, A.; Fujita, T.; Harima, Y. Chem. Pharm. Bull. 1982, 30, 172-179.
http://dx.doi.org/10.1248/cpb.30.172
[34]. Daves, G. D.; Robins, R. K.; Cheng, C. C. J. Am. Chem. Soc. 1962, 84, 1724-1729.
http://dx.doi.org/10.1021/ja00868a046
[35]. Sakuma, Y.; Nagamatsu, T.; Hashiguchi, Y.; Yoneda, F. Chem. Pharm. Bull. 1984, 32, 851-859.
http://dx.doi.org/10.1248/cpb.32.851
[36]. Yoneda, F.; Nakagawa, K. J. Chem. Soc. Chem. Comm. 1980, 1980, 878-879.
[37]. Yoneda, F.; Higuchi, M.; Kawamura, M.; Nitta, Y. Heterocycles 1978, 9, 1571-1576.
http://dx.doi.org/10.3987/R-1978-11-1571
[38]. Fugmann, B.; Lang-Fugmann, S.; Steglich, W. RÖMPP-Lexikon Naturstoffe, 6th edition, Georg Thieme, Stuttgart, 1997.
How to cite
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.7.1.73-80.1371
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2016, 7(1), 73-80 | doi: https://doi.org/10.5155/eurjchem.7.1.73-80.1371 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • 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 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.