European Journal of Chemistry

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

Crossmark


Main Article Content

Fatma Ahmed Abo Elsoud
Mohamed Abd-Elmonem
Mohamed Abo Elsebaa
Kamal Usef Sadek

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.


icon graph This Abstract was viewed 1596 times | icon graph Article PDF downloaded 668 times

How to Cite
(1)
Abo Elsoud, F. A.; Abd-Elmonem, M.; Abo Elsebaa, M.; Sadek, K. U. 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, 166-170.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

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 © 2024 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).