European Journal of Chemistry

A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination

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Published: Mar 31, 2016
DOI: https://doi.org/10.5155/eurjchem.7.1.73-80.1371
Keywords:
Azaenamine, Michael addition, Cyanoacetylurea, 4-Deazatoxoflavin, α-Cyanoacrylamide, HMBC spectroscopy
Section
Research Article
Issue
Vol. 7 No. 1 (2016): March 2016
Dates
Received 2015-11-23
Accepted 2015-12-19
Published 2016-03-31


Main Article Content

Amr Mohamed Abdelmoniem
Department of Chemistry, Faculty of Science, Cairo University, 12613 Giza, Egypt
Said Ahmed Soliman Ghozlan
Department of Chemistry, Faculty of Science, Cairo University, 12613 Giza, Egypt
Holger Butenschön
Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany
Ismail Abdelshafy Abdelhamid
Department of Chemistry, Faculty of Science, Cairo University, 12613 Giza, Egypt

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.

 


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Abdelmoniem, A. M.; Ghozlan, S. A. S.; Butenschön, H.; Abdelhamid, I. A. A Facile Synthesis of 3-Amino-2,5-Dihydropyridazines and 4-Deazatoxoflavin Analogues via [3+3] Atom Combination. Eur. J. Chem. 2016, 7, 73-80.

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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.

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