European Journal of Chemistry 2019, 10(2), 166-170 | doi: https://doi.org/10.5155/eurjchem.10.2.166-170.1851 | Get rights and content

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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 | Revised: 19 May 2019 | Accepted: 20 May 2019 | Published: 30 Jun 2019 | Issue Date: June 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.


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Keywords


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

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DOI: 10.5155/eurjchem.10.2.166-170.1851

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Funding information


Deraya University, Minia 61768, Egypt

Citations

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[1]. Morteza Ziyaadini, Nabi Nemat-Bakhsh, Seyyed Jalal Roudbaraki, Majid Ghashang
Zn2SnO4-SnO2 Nano-Composite Promoted Ultrasonic-Assisted Synthesis of Pyran Derivatives
Polycyclic Aromatic Compounds  42(2), 460, 2022
DOI: 10.1080/10406638.2020.1743328
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[2]. Kamal Usef Sadek, Ramadan Ahmed Mekheimer, Mohamed Abd‐Elmonem, Mohamed Hilmy Elnagdi
Recent developments in the utility of Zn(L‐proline)2 as benign and recyclable metallo‐organocatalyst in organic synthesis
Applied Organometallic Chemistry  34(2), , 2020
DOI: 10.1002/aoc.5315
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[3]. Mohammad Suhail, Sofi Danish Mukhtar, Imran Ali, Ariba Ansari, Saiyam Arora
Theoretical DFT study of Cannizzaro reaction mechanism: A mini perspective
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[4]. Anupam Sarkar, Subhradeep Mistry, Srinivasan Natarajan
Friedländer, Knoevenagel, and Michael Reactions Employing the Same MOF: Synthesis, Structure, and Heterogeneous Catalytic Studies of ([Zn(1,4-NDCA)(3-BPDB)0.5]·(DMF)(MeOH) and [Cd4(1,4-NDCA)4(3-BPDB)4]·2(DMF)
The Journal of Physical Chemistry C  125(49), 27230, 2021
DOI: 10.1021/acs.jpcc.1c08474
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[5]. Biplob Borah, Kartikey Dhar Dwivedi, L. Raju Chowhan
Review on Synthesis and Medicinal Application of Dihydropyrano[3,2-b]Pyrans and Spiro-Pyrano[3,2-b]Pyrans by Employing the Reactivity of 5-Hydroxy-2-(Hydroxymethyl)-4H-Pyran-4-One
Polycyclic Aromatic Compounds  42(9), 5893, 2022
DOI: 10.1080/10406638.2021.1962923
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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. 30 Nov. 2023
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)

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