European Journal of Chemistry 2016, 7(1), 73-80. doi:10.5155/eurjchem.7.1.73-80.1371

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, Accepted: 19 Dec 2015, Published: 31 Mar 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.

 


Keywords


Azaenamine; Michael addition; Cyanoacetylurea; 4-Deazatoxoflavin; α-Cyanoacrylamide; HMBC spectroscopy

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.7.1.73-80.1371

Article Metrics


This Abstract was viewed 521 times | PDF Article downloaded 227 times

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  , , 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


Abdelmoniem, A.; Ghozlan, S.; Butenschön, H.; Abdelhamid, I. Eur. J. Chem. 2016, 7(1), 73-80. doi:10.5155/eurjchem.7.1.73-80.1371
Abdelmoniem, A.; Ghozlan, S.; Butenschön, H.; Abdelhamid, I. A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination. Eur. J. Chem. 2016, 7(1), 73-80. doi:10.5155/eurjchem.7.1.73-80.1371
Abdelmoniem, A., Ghozlan, S., Butenschön, H., & Abdelhamid, I. (2016). A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination. European Journal of Chemistry, 7(1), 73-80. doi:10.5155/eurjchem.7.1.73-80.1371
Abdelmoniem, Amr, Said Ahmed Soliman Ghozlan, Holger Butenschön, & Ismail Abdelshafy Abdelhamid. "A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination." European Journal of Chemistry [Online], 7.1 (2016): 73-80. Web. 23 Oct. 2019
Abdelmoniem, Amr, Ghozlan, Said, Butenschön, Holger, AND Abdelhamid, Ismail. "A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination" European Journal of Chemistry [Online], Volume 7 Number 1 (31 March 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.1.73-80.1371

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.