European Journal of Chemistry 2010, 1(4), 252-258 | doi: https://doi.org/10.5155/eurjchem.1.4.252-258.211 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

Chitosan as an eco-friendly heterogeneous catalyst for Michael type addition reactions. A simple and efficient route to pyridones and phthalazines


Khaled Khalil (1) , Hamad Al-Matar (2,*) , Mohamed Elnagdi (3)

(1) Chemistry Department, Faculty of Science, Cairo University, Giza, EG-12613, Egypt
(2) Chemistry Department, Faculty of Science, University of Kuwait, KW-13060, Kuwait
(3) Chemistry Department, Faculty of Science, University of Kuwait, KW-13060, Kuwait
(*) Corresponding Author

Received: 21 Jul 2010 | Revised: 30 Nov 2010 | Accepted: 25 Jul 2010 | Published: 22 Dec 2010 | Issue Date: December 2010

Abstract


Depending on their nature, nitrile activated methylene compounds add readily to β-enaminones in presence of chitosan to yield dienamides, pyridones or pyridine thiones. The dienamides, formed in this manner, can be readily converted to pyridones by stirring in refluxing acetic acid. Reaction of pyridazinones with a mixture containing benzaldehyde, malononitrile and chitosan affords phthalazines that are also produced by reaction of pyridazinone with benzylidene-malononitrile.

1_4_252_258_800


Keywords


Chitosan; Enaminone; Michael addition; Pyridone; Pthalazine; Benzylidene

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.1.4.252-258.211

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 1933 times | PDF Article downloaded 501 times

Funding information


Kuwait University - Research Adminstration

Citations

/


[1]. Ahmed El‐Mekabaty, Hanem M. Awad
Convenient synthesis of novel sulfonamide derivatives as promising anticancer agents
Journal of Heterocyclic Chemistry  57(3), 1123, 2020
DOI: 10.1002/jhet.3849
/


[2]. Maria A. Vodolazhenko, Nikolay Yu. Gorobets, Sergey A. Yermolayev, Vladimir V. Musatov, Valentin A. Chebanov, Sergey M. Desenko
Application of stable fused dienolates for diversity oriented synthesis of 2,5-dioxo-5,6,7,8-tetrahydro-2H-chromene-3-carboxamides
RSC Adv.  2(3), 1106, 2012
DOI: 10.1039/C1RA00723H
/


[3]. Abdulaziz Alnajjar, Marzouq Alsaiedi, Morsy Ahmed El-Apasery
An efficient route for the synthesis of some monoazo disperse dyes derived from nicotinic acid derivatives
European Journal of Chemistry  4(1), 53, 2013
DOI: 10.5155/eurjchem.4.1.53-57.733
/


[4]. Rajender S. Varma
Biomass-Derived Renewable Carbonaceous Materials for Sustainable Chemical and Environmental Applications
ACS Sustainable Chemistry & Engineering  7(7), 6458, 2019
DOI: 10.1021/acssuschemeng.8b06550
/


[5]. Fatereh Asghari-Haji, Kurosh Rad-Moghadam, Nosrat O. Mahmoodi
An efficient approach to bis-benzoquinonylmethanes on water under catalysis of the bio-derived O-carboxymethyl chitosan
RSC Advances  6(33), 27388, 2016
DOI: 10.1039/C5RA26580K
/


[6]. Khaled Khalil, Hamad Al-Matar
Chitosan Based Heterogeneous Catalyses: Chitosan-Grafted-Poly(4-Vinylpyridne) as an Efficient Catalyst for Michael Additions and Alkylpyridazinyl Carbonitrile Oxidation
Molecules  18(5), 5288, 2013
DOI: 10.3390/molecules18055288
/


[7]. Khaled D. Khalil, Enas I. Ibrahim, Fakhreia A. Al-Sagheer
A novel, efficient, and recyclable biocatalyst for Michael addition reactions and its iron(iii) complex as promoter for alkyl oxidation reactions
Catalysis Science & Technology  6(5), 1410, 2016
DOI: 10.1039/C5CY01034A
/


[8]. Sara Zhaleh, Nourallah Hazeri, Mohammad Reza Faghihi, Malek Taher Maghsoodlou
Chitosan: a sustainable, reusable and biodegradable organocatalyst for green synthesis of 1,4-dihydropyridine derivatives under solvent-free condition
Research on Chemical Intermediates  42(12), 8069, 2016
DOI: 10.1007/s11164-016-2579-7
/


[9]. Amit Kumar, Chetananda Patel, Pooja Patil, Shivam Vyas, Abha Sharma
Chemoselective synthesis of bis(indolyl)methanes using sulfonic acid-functionalized chitosan
Chemical Papers  73(12), 3095, 2019
DOI: 10.1007/s11696-019-00846-2
/


[10]. Sayed Riyadh, Khaled Khalil, Ateyatallah Aljuhani
Chitosan-MgO Nanocomposite: One Pot Preparation and Its Utility as an Ecofriendly Biocatalyst in the Synthesis of Thiazoles and [1,3,4]thiadiazoles
Nanomaterials  8(11), 928, 2018
DOI: 10.3390/nano8110928
/


[11]. Sobhi M. Gomha, Sayed M. Riyadh, Elmahdi A. Mahmmoud, Mahmoud M. Elaasser
Synthesis and anticancer activity of arylazothiazoles and 1,3,4-thiadiazoles using chitosan-grafted-poly(4-vinylpyridine) as a novel copolymer basic catalyst
Chemistry of Heterocyclic Compounds  51(11-12), 1030, 2015
DOI: 10.1007/s10593-016-1815-9
/


[12]. Ebtesam Abdul Aziz Hafez, Saleh Mohammed Al-Mousawi, Moustafa Sherief Moustafa, Kmal Usef Sadek, Mohamed Hilmy Elnagdi
Green methodologies in organic synthesis: recent developments in our laboratories
Green Chemistry Letters and Reviews  6(3), 189, 2013
DOI: 10.1080/17518253.2012.740078
/


[13]. Sayed M. Riyadh, Sobhi M. Gomha, Elmahdi A. Mahmmoud, Mahmoud M. Elaasser
Synthesis and Anticancer Activities of Thiazoles, 1,3-Thiazines, and Thiazolidine Using Chitosan-Grafted-Poly(vinylpyridine) as Basic Catalyst
HETEROCYCLES  91(6), 1227, 2015
DOI: 10.3987/COM-15-13210
/


[14]. Pratibha Rai, Madhulika Srivastava, Jaya Singh, Jagdamba Singh
Chitosan/ionic liquid forms a renewable and reusable catalyst system used for the synthesis of highly functionalized spiro derivatives
New Journal of Chemistry  38(7), 3181, 2014
DOI: 10.1039/c3nj01545a
/


[15]. Olivier Mahé, Jean-François Brière, Isabelle Dez
Chitosan: An Upgraded Polysaccharide Waste for Organocatalysis
European Journal of Organic Chemistry  2015(12), 2559, 2015
DOI: 10.1002/ejoc.201403396
/


[16]. Zeba N. Siddiqui, Kulsum Khan
Friedlander synthesis of novel benzopyranopyridines in the presence of chitosan as heterogeneous, efficient and biodegradable catalyst under solvent-free conditions
New Journal of Chemistry  37(5), 1595, 2013
DOI: 10.1039/c3nj00069a
/


[17]. Hamad M. Al-Matar, Khaled D. Khalil, Mona F. Al-Kanderi, Mohamed H. Elnagdi
Studies on 3-Oxoalkanenitriles: Novel Rearrangement Reactions Observed in Studies of the Chemistry of 3-Heteroaroyl-3-Oxoalkanenitriles as Novel Routes to 2-Dialkylaminopyridines
Molecules  17(1), 897, 2012
DOI: 10.3390/molecules17010897
/


[18]. Safura Zahedi, Javad Safaei Ghomi, Hossein Shahbazi-Alavi
Preparation of chitosan nanoparticles from shrimp shells and investigation of its catalytic effect in diastereoselective synthesis of dihydropyrroles
Ultrasonics Sonochemistry  40, 260, 2018
DOI: 10.1016/j.ultsonch.2017.07.023
/


[19]. Premchand B. Shelke, Suraj N. Mali, Hemchandra K. Chaudhari, Amit P. Pratap
Chitosan hydrochloride mediated efficient, green catalysis for the synthesis of perimidine derivatives
Journal of Heterocyclic Chemistry  56(11), 3048, 2019
DOI: 10.1002/jhet.3700
/


[20]. Pramod K. Sahu, Praveen K. Sahu, Sushil K. Gupta, Dau D. Agarwal
Chitosan: An Efficient, Reusable, and Biodegradable Catalyst for Green Synthesis of Heterocycles
Industrial & Engineering Chemistry Research  53(6), 2085, 2014
DOI: 10.1021/ie402037d
/


References

[1]. Niola, F.; Basora, N.; Chornet, E.; Vidal, P. F. Carbohyd. Res.1993, 238, 1-9.
doi:10.1016/0008-6215(93)87001-9

[2]. Bader, H. J.; Birkholz, E. Praxis der Naturwissenschaften,Chemie1996, 45(6), 24-30.

[3]. Rege, P. R.; Block, L. H. Carbohyd. Res.1999, 321, 235-245.
doi:10.1016/S0008-6215(99)00172-X

[4]. Gomha, S. M.; Riyadh, S. M. Arkivoc2009, 11, 58-68.

[5]. Al-Matar, H. M.; Khalil, K. D.; Meier, H.; Kolshorn, H.; Elnagdi, M. H. Arkivoc 2008, 16, 288-301.

[6]. Alnajjar, A.; Abdelkhalik, M. M.; Al-Enezi, A.; Elnagdi, M. H. Molecules2009, 14(1), 68-77.
doi:10.3390/molecules14010068
PMid:19127238

[7]. Al-Saleh, B.; El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. J. Heterocyclic Chem.2005, 42(4), 563-566.
doi:10.1002/jhet.5570420414

[8]. Schmidt, U.; Kubitzek, H. Chemische Berichte1960, 93,1559-65.
doi:10.1002/cber.19600930716

[9]. Boatman, S.; Harris, T. M.; Hauser, C. R. J. Org. Chem.1965, 30(11), 3593-7.
doi:10.1021/jo01022a003

[10]. Ghozlan, S. A. S.; Abdelhamid, I. A.; Elnagdi, M. H. Arkivoc2006, 13, 147-157.

[11]. Al-Mousawi, S. M.; Moustafa, M. S.; Abdelkhalik, M. M.; Elnagdi, M. H. Arkivoc2009, 11, 1-10.

[12]. Al-Omran, F.; Al-Awadi, N.; Abdelkhalik, M. M.; Kaul, K.; Elkhair, A. A.; Elnagdi, M. H. J. Chem. Res. (S) 1997, 84, 601-613.

[13]. Abdelrazek, F. M.; Elsayed, A. N. J. Heterocyclic Chem. 2009, 46, 949-953.
doi:10.1002/jhet.181

[14]. Gorobets, N. Y.; Sedash, Y. V.; Shishkina, S. V.; Shishkin, O. V.; Yermolayev, S. A.; Desenko, S. M. Arkivoc2009, 13, 23-30.

[15]. Abdelrazek, F. M.; Michael, F. A. J. Heterocyclic Chem. 2006, 43(1), 7-10.
doi:10.1002/jhet.5570430102

[16]. Al-Mousawi, S.; Moustafa, M. S.; Elnagdi, M. H. Arkivoc2008, 10, 17-25.

[17]. Al-Saleh, B.; Hilmy, Noha M.; El-Apasery, M. A.; Elnagdi, M. H. J. Heterocyclic Chem.2006, 43(6), 1575-1581.
doi:10.1002/jhet.5570430622

[18]. Mogilaiah, K.; Rani, J. Uma. Indian J. Heterocycl. Chem.2003, 13(2), 169-170.

[19]. Xu, Da-Zh.; Liu,Y.; Shi S.; Wang, Y.GreenChem.2010, 12, 514-517.
doi:10.1039/b918595j

How to cite


Khalil, K.; Al-Matar, H.; Elnagdi, M. Eur. J. Chem. 2010, 1(4), 252-258. doi:10.5155/eurjchem.1.4.252-258.211
Khalil, K.; Al-Matar, H.; Elnagdi, M. Chitosan as an eco-friendly heterogeneous catalyst for Michael type addition reactions. A simple and efficient route to pyridones and phthalazines. Eur. J. Chem. 2010, 1(4), 252-258. doi:10.5155/eurjchem.1.4.252-258.211
Khalil, K., Al-Matar, H., & Elnagdi, M. (2010). Chitosan as an eco-friendly heterogeneous catalyst for Michael type addition reactions. A simple and efficient route to pyridones and phthalazines. European Journal of Chemistry, 1(4), 252-258. doi:10.5155/eurjchem.1.4.252-258.211
Khalil, Khaled, Hamad Al-Matar, & Mohamed Elnagdi. "Chitosan as an eco-friendly heterogeneous catalyst for Michael type addition reactions. A simple and efficient route to pyridones and phthalazines." European Journal of Chemistry [Online], 1.4 (2010): 252-258. Web. 28 Mar. 2020
Khalil, Khaled, Al-Matar, Hamad, AND Elnagdi, Mohamed. "Chitosan as an eco-friendly heterogeneous catalyst for Michael type addition reactions. A simple and efficient route to pyridones and phthalazines" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

DOI Link: https://doi.org/10.5155/eurjchem.1.4.252-258.211

| | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2010, 1(4), 252-258 | doi: https://doi.org/10.5155/eurjchem.1.4.252-258.211 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  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 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort