European Journal of Chemistry 2019, 10(2), 166-170. doi:10.5155/eurjchem.10.2.166-170.1851

Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives


Fatma Ahmed Abo Elsoud (1) orcid , Mohamed Abd-Elmonem (2) orcid , Mohamed Abo Elsebaa (3,*) orcid , Kamal Usef Sadek (4) orcid

(1) Pharmaceutical Chemistry Department, Faculty of Pharmacy, Deraya University, Minia 61768, Egypt
(2) Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
(3) Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
(4) Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
(*) Corresponding Author

Received: 24 Mar 2019, Accepted: 20 May 2019, Published: 30 Jun 2019

Abstract


Efficient synthesis of non-annulated 2-amino-4H-pyrans and 2-amino-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives, which are biologically relevant heterocycles is achieved, utilizing a domino three-component reaction of ethyl acetoacetate or kojic acid with aromatic aldehydes and malononitrile catalyzed by Zn(L-proline)2 as reusable organometallic catalyst. The process exhibits high atom economy, short reaction time, simple work up, high yields and environmentally friendly nature. Excellent yields of the targeted molecules have been obtained.


Keywords


Recyclability; Zn(L-proline)2; Pyrans synthesis; Lewis acid catalyst; Environmentally friendly nature; Domino three-component reaction

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.10.2.166-170.1851

Article Metrics


This Abstract was viewed 37 times | PDF Article downloaded 34 times

References

[1]. Xie, L.; Takeuchi, Y.; Cosentino, L. M.; Mcphail, A. T.; Lee, K. H. J. Med. Chem. 2001, 44, 664-671.
https://doi.org/10.1021/jm000070g

[2]. Emmadi, N. R.; Atmakur, K.; Chityal, G. K.; Pombala, S.; Nanubolu, J. B. Bioorg. Med. Chem. Lett. 2012, 22, 7261-7264.
https://doi.org/10.1016/j.bmcl.2012.09.018

[3]. Kumar, A.; Maurya, R. A.; Sharma, S.; Ahmad, P.; Singh, A. B.; Bhatia, G.; Srivastava, A. K. Bioorg. Med. Chem. Lett. 2009, 19, 6446-6451.
https://doi.org/10.1016/j.bmcl.2009.09.031

[4]. Hume, P. A.; Sperry, J.; Brimble, M. A. Org. Biomol. Chem. 2011, 9, 5423-5430.
https://doi.org/10.1039/c1ob05595j

[5]. Xu, Z. Q.; Pupek, K.; Suling, W. J.; Fnuche, L.; Flavin, M. T. Bioorg. Med. Chem. 2006, 14, 4610-4626.
https://doi.org/10.1016/j.bmc.2006.02.017

[6]. Mahlau, M.; Fernandes, R. A.; Brückner, R. Eur. J. Org. Chem. 2011, 2011, 4765-4772.
https://doi.org/10.1002/ejoc.201190066

[7]. Ellis, G. P., Chromenes, chromanones, and chromones. In: The Chemistry of Heterocyclic Compounds Chromenes, Weissberger, A. and Taylor, E. C.; John Wiley, New York, NY, USA, Chapter 2, P11-139, 1977.
https://doi.org/10.1002/9780470187012

[8]. Hafez, E. A.; Elnagdi, M. H.; Elagamey, A. G. A.; El-Taweel, F. M. M. A. Heterocycles 1987, 26, 903-907.
https://doi.org/10.3987/R-1987-04-0903

[9]. Brahmachari, G.; Banerjee, B. Acs Sustain. Chem. Eng. 2014, 2, 411-422.
https://doi.org/10.1021/sc400312n

[10]. Meng, X. X.; Du, B. X.; Zhao, B.; Li, Y. L.; Chen, C. F. J. Chem. Res. 2013, 37, 638-641.
https://doi.org/10.3184/174751913X13796142561782

[11]. Litvinov, Y. M.; Shestopalov, A. M. Adv. Heterocycl. Chem. 2001, 103, 175-260.
https://doi.org/10.1016/B978-0-12-386011-8.00003-4

[12]. Azarifar, D.; Ebrahimiasl, H.; Karamian, R.; Ahmadi-Khoei, M. J. Iran. Chem. Soc. 2018, Vol. 16.

[13]. Sadeghi, B.; Nezhad, P. F.; Hashemian, S. J. Chem. Res. 2014, 38, 54-57.
https://doi.org/10.3184/174751914X13866053657371

[14]. Baghbanian, S. M. RSC Adv. 2014, 4, 59397-59404.
https://doi.org/10.1039/C4RA10537K

[15]. Heravi, M. M.; Ghods, A.; Bakhtiari, K. Synth. Commun. 2010, 40, 1927-1931.
https://doi.org/10.1080/00397910903174390

[16]. Layek, S.; Agrahari, B.; Kumari, S.; Anuradha; Pathak, D. D. Catal. Lett. 2018, 148, 2675-2682.
https://doi.org/10.1007/s10562-018-2449-6

[17]. Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
https://doi.org/10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U

[18]. Yazdani-Elah-Abadi, A.; Maghsoodlou, M. T.; Mohebat, R.; Heydari, R. J. Chem. Sci. 2017, 192, 691-698.
https://doi.org/10.1007/s12039-017-1292-4

[19]. Benzekri, Z.; Serrar, H.; Boukhris, S.; Sallek, B.; Souizi, A. Current Chem. Lett. 2016, 5, 99-108.
https://doi.org/10.5267/j.ccl.2016.4.001

[20]. Kataev, E. A.; Reddy, M. R.; Reddy, G. N.; Reddy, V. H.; Reddy, C. S.; Reddy, B. V. S. New J. Chem. 2015, 40, 1639-1697.
https://doi.org/10.1039/C5NJ01902H

[21]. Hameed, A. A.; Ahmed, E. K.; Abdel Fattah, A. A.; Andrade, C. K. Z.; Sadek, K. U. Res. Chem. Intermed. 2017, 43, 5523-5533.
https://doi.org/10.1007/s11164-017-2944-1

[22]. Abdel Hamid, A.; Abd-Elmonem, M.; Hayallah, A. M.; Abo Elsoud, F. A.; Sadek, K. U. Chem. Select 2017, 2, 10689-10693.
https://doi.org/10.1002/slct.201702011

[23]. Sadek, K. U.; Hameed, A. M. A.; Mekheimer, R. A.; Abd-Elmonem, M.; Elnagdi, M. H. Curr. Microw. Chem. 2016, 3, 227-232.
https://doi.org/10.2174/2213335602666150917011405

[24]. Sadek, K. U.; Shaker, R. M.; Elrady, M. A.; Elnagdi, M. H. Tetrahedron Lett. 2010, 51, 6319-6321.
https://doi.org/10.1016/j.tetlet.2010.09.114

[25]. Mekheimer, R. A.; Hameed, A. A.; Sadek, K. U. Green Chem. 2008, 10, 592-593.
https://doi.org/10.1039/b715126h

[26]. Sadek, K. U.; Selim, M. A.; Alnajjar, A. -A.; Atallah, M.; Elnagdi, M. H. Eur. J. Chem. 2016, 7, 468-472.
https://doi.org/10.5155/eurjchem.7.4.468-472.1508

[27]. Kidwai, M.; Jian, A.; Bhardwaj, S. Catal. Lett. 2011, 141, 183-190.
https://doi.org/10.1007/s10562-010-0451-8

[28]. Tahmassebi, D.; Blevins, J. E.; Gerardot, S. S. Appl. Organomet. Chem. 2019, 33, e4807.
https://doi.org/10.1002/aoc.4807

[29]. Elnagdi, N. M. H.; Al-Hobkany, N. S. Molecules 2012, 17, 4300-4312.
https://doi.org/10.3390/molecules17044300


How to cite


Abo Elsoud, F.; Abd-Elmonem, M.; Abo Elsebaa, M.; Sadek, K. Eur. J. Chem. 2019, 10(2), 166-170. doi:10.5155/eurjchem.10.2.166-170.1851
Abo Elsoud, F.; Abd-Elmonem, M.; Abo Elsebaa, M.; Sadek, K. Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives. Eur. J. Chem. 2019, 10(2), 166-170. doi:10.5155/eurjchem.10.2.166-170.1851
Abo Elsoud, F., Abd-Elmonem, M., Abo Elsebaa, M., & Sadek, K. (2019). Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives. European Journal of Chemistry, 10(2), 166-170. doi:10.5155/eurjchem.10.2.166-170.1851
Abo Elsoud, Fatma, Mohamed Abd-Elmonem, Mohamed Abo Elsebaa, & Kamal Usef Sadek. "Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives." European Journal of Chemistry [Online], 10.2 (2019): 166-170. Web. 20 Jul. 2019
Abo Elsoud, Fatma, Abd-Elmonem, Mohamed, Abo Elsebaa, Mohamed, AND Sadek, Kamal. "Zn(L-proline)2: An efficient and reusable organocatalyst for the synthesis of polyfunctionally substituted pyrans and 2-amino-4-aryl-8-oxo-4,8-dihydropyrano[3,2-b]pyran derivatives" European Journal of Chemistry [Online], Volume 10 Number 2 (30 June 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.2.166-170.1851

Refbacks

  • There are currently no refbacks.




Copyright (c) 2019 Authors

Creative Commons License
This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/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 (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).


© 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.