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

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Published: Jun 30, 2019
DOI: https://doi.org/10.5155/eurjchem.10.2.166-170.1851
Keywords:
Recyclability, Zn(L-proline)2, Pyrans synthesis, Lewis acid catalyst, Environmentally friendly nature, Domino three-component reaction
Section
Research Article
Issue
Vol. 10 No. 2 (2019): June 2019
Dates
Received 2019-03-24
Accepted 2019-05-20
Published 2019-06-30
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Fatma Ahmed Abo Elsoud
Pharmaceutical Chemistry Department, Faculty of Pharmacy, Deraya University, Minia 61768, Egypt
http://orcid.org/0000-0002-3650-0379
Mohamed Abd-Elmonem
Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
http://orcid.org/0000-0002-4808-1650
Mohamed Abo Elsebaa
Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
http://orcid.org/0000-0001-8810-9438
Kamal Usef Sadek
Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt
http://orcid.org/0000-0003-4342-5394

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.


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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.

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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

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Deraya University, Minia 61768, Egypt
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