Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
Green methodologies in organic synthesis: Microwave assisted solvent- and catalyst-free synthesis of enaminones and their conversion into 1,3,5-trisubstituted benzenes as well as 3-aroyl-6-substituted pyridines
Morsy Ahmed El-Apasery (1)
, Saleh Mohamed Al-Mousawi (2,*) , Mohamed Helmy Elnagdi (3) (1) Department of Chemistry, Faculty of Science, Kuwait University, Safat, 13060, Kuwait
(2) Department of Chemistry, Faculty of Science, Kuwait University, Safat, 13060, Kuwait
(3) Department of Chemistry, Faculty of Science, Kuwait University, Safat, 13060, Kuwait
(*) Corresponding Author
Received: 03 Aug 2010 | Revised: 24 Feb 2011 | Accepted: 16 Nov 2010 | Published: 30 Jun 2011 | Issue Date: June 2011
Abstract
Enaminones were obtained in good yields via condensing methyl ketones with (N,N-dimethylformamide dimethyl acetal) DMF-DMA under microwave irradiation in absence of solvent. These enaminones were readily converted into 1,3,5-trisubstituted benzenes. Reacting enaminones in presence of ammonium acetate has afforded pyridine derivatives.
Keywords
Enaminone; Solvent-free; Green chemistry; Dye intermediates; Microwave irradiation; 1,3,5-trisubstituted benzenes
DOI: 10.5155/eurjchem.2.2.168-172.228
Links for Article
| | | | |
| | | | | | |
Related Articles
Article Metrics
This Abstract was viewed 1120 times |
PDF Article downloaded 377 times
Funding information
Kuwait University
Citations
[1]. Utpalparna Kalita, Shunan Kaping, Revinus Nongkynrih, Melboureen Sunn, Ivee Boiss, Laishram Indira Singha, Jai Narain Vishwakarma
Synthesis, structure elucidation, and anti-inflammatory/anti-cancer/anti-bacterial activities of novel (Z)-3-adamantyl-1-aryl-prop/but-2-en-1-ones
Medicinal Chemistry Research 24(1), 32, 2015
DOI: 10.1007/s00044-014-1086-x
[2]. Jie-Ping Wan, Yong Gao
Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines
The Chemical Record 16(3), 1164, 2016
DOI: 10.1002/tcr.201500296
[3]. Subrata Das, Rupak Banik, Brajesh Kumar, Subhadip Roy, Noorussabah, Khursheed Amhad, Pradip K. Sukul
A Green Approach for Organic Transformations Using Microwave Reactor
Current Organic Synthesis 16(5), 730, 2019
DOI: 10.2174/1570179416666190412160048
[4]. Claudio G. Lima–Junior, Mário L.A.A. Vasconcellos
Morita–Baylis–Hillman adducts: Biological activities and potentialities to the discovery of new cheaper drugs
Bioorganic & Medicinal Chemistry 20(13), 3954, 2012
DOI: 10.1016/j.bmc.2012.04.061
[5]. 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
References
[1]. Zhu, S.; Zhao, K.; Su, X.; Ji, S. Synth. Commun. 2009, 39, 1355-1366.
doi:10.1080/00397910802527714
[2]. Loghmani-Khouzani, H.; Sabzyan, H; Rezaei-Pooranari, A. Dyes pigments 2008, 76, 447-454.
doi:10.1016/j.dyepig.2006.10.003
[3]. Riyadh, S. M.; Abdelhamid, I. A.; Al-Matar, H. M.; Hilmy, N. H.; Elnagdi, M. H. Heterocycles 2008, 75, 1849-1905.
doi:10.3987/REV-07-625
[4]. Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433-2480.
doi:10.1021/cr020093y
PMid:15137796
[5]. Sheikhshoaie, I. F; Walter M. F. Curr. Org. Chem. 2009, 13(2), 149-171.
doi:10.2174/138527209787193747
[6]. Macho, S.; Miguel, D.; Neo, A. G.; Rodriguez, T.; Torroba, T. Chem. Commun. 2005, 3, 334-336.
doi:10.1039/b412632g
PMid:15645028
[7]. De Oliveira, H. C. B.; Fonseca, T. L.; Castro, M. A.; Amaral, O. A. V.; Cunha, S. J. Chem. Phys. 2003, 119(16), 8417-8424.
[8]. Ghozlan S. A. S; Abdelhamid, I. A.; Gaber, H.; Elnagdi, M. H. J. Heterocycl. Chem. 2005, 42, 1185-1189.
doi:10.1002/jhet.5570420623
[9]. Al-Saleh, B.; Makhseed, S.; Hassaneen, H. M. E.; Elnagdi, M. H. Synthesis, 2006, 59-62.
[10]. Murahashi, S.; Mitsue, Y.; Tsumiyama, T. Bull. Chem. Soc. Jap. 1987, 60(9), 3285-3290.
doi:10.1246/bcsj.60.3285
[11]. Braibante, M. E. F.; Braibante, H. T. S.; Rosso, G. B.; Oriques, D. A. J. Braz. Chem. Soc. 2003, 14, 994-997.
doi:10.1590/S0103-50532003000600016
[12]. Braibante, H. T. S.; Braibante, M. E. F.; Morel, A. F.; Costa. C. C.; Lima, M. G. J. Braz. Chem. Soc. 2006, 17, 184-188.
doi:10.1590/S0103-50532006000100026
[13]. Rechsteiner, B.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1993, 34, 5071-5074.
doi:10.1016/S0040-4039(00)60678-0
[14]. Lee, D. H.; Park, S. E.; Cho, K.; Kim, Y.; Athar, T.; Lee, I. M. Tetrahedron Lett. 2007, 48, 8281-8284.
doi:10.1016/j.tetlet.2007.09.143
[15]. Andrade, C. K. Z.; Barreto, A. S.; Silva, W. A. Arkivoc 2008, 12, 226-232.
[16]. Al-Mousawi, S. M.; El-Apasery, M. A.; Elnagdi, M. H. Molecules 2010, 15, 58-67.
doi:10.3390/molecules15010058
PMid:20110871
[17]. Al-Saleh, B.; El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. J. Heterocycl. Chem. 2005, 42(4), 563-566.
doi:10.1002/jhet.5570420414
[18]. El-Dusouqui, O. M. E.; Abdelkhalik, M. M.; Al-Awadi, N. A.; Dib, H. H.; George, B. J.; Elnagdi, M. H. J. Chem. Res. 2006, 5, 295-302.
[19]. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Rosa, F. A.; Marzari, M. R. B.; Zanatta, N.; Bonacorso, H. G. Catalysis Commun. 2008, 9(6), 1375-1378.
doi:10.1016/j.catcom.2007.11.037
doi:10.1080/00397910802527714
[2]. Loghmani-Khouzani, H.; Sabzyan, H; Rezaei-Pooranari, A. Dyes pigments 2008, 76, 447-454.
doi:10.1016/j.dyepig.2006.10.003
[3]. Riyadh, S. M.; Abdelhamid, I. A.; Al-Matar, H. M.; Hilmy, N. H.; Elnagdi, M. H. Heterocycles 2008, 75, 1849-1905.
doi:10.3987/REV-07-625
[4]. Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433-2480.
doi:10.1021/cr020093y
PMid:15137796
[5]. Sheikhshoaie, I. F; Walter M. F. Curr. Org. Chem. 2009, 13(2), 149-171.
doi:10.2174/138527209787193747
[6]. Macho, S.; Miguel, D.; Neo, A. G.; Rodriguez, T.; Torroba, T. Chem. Commun. 2005, 3, 334-336.
doi:10.1039/b412632g
PMid:15645028
[7]. De Oliveira, H. C. B.; Fonseca, T. L.; Castro, M. A.; Amaral, O. A. V.; Cunha, S. J. Chem. Phys. 2003, 119(16), 8417-8424.
[8]. Ghozlan S. A. S; Abdelhamid, I. A.; Gaber, H.; Elnagdi, M. H. J. Heterocycl. Chem. 2005, 42, 1185-1189.
doi:10.1002/jhet.5570420623
[9]. Al-Saleh, B.; Makhseed, S.; Hassaneen, H. M. E.; Elnagdi, M. H. Synthesis, 2006, 59-62.
[10]. Murahashi, S.; Mitsue, Y.; Tsumiyama, T. Bull. Chem. Soc. Jap. 1987, 60(9), 3285-3290.
doi:10.1246/bcsj.60.3285
[11]. Braibante, M. E. F.; Braibante, H. T. S.; Rosso, G. B.; Oriques, D. A. J. Braz. Chem. Soc. 2003, 14, 994-997.
doi:10.1590/S0103-50532003000600016
[12]. Braibante, H. T. S.; Braibante, M. E. F.; Morel, A. F.; Costa. C. C.; Lima, M. G. J. Braz. Chem. Soc. 2006, 17, 184-188.
doi:10.1590/S0103-50532006000100026
[13]. Rechsteiner, B.; Texier-Boullet, F.; Hamelin, J. Tetrahedron Lett. 1993, 34, 5071-5074.
doi:10.1016/S0040-4039(00)60678-0
[14]. Lee, D. H.; Park, S. E.; Cho, K.; Kim, Y.; Athar, T.; Lee, I. M. Tetrahedron Lett. 2007, 48, 8281-8284.
doi:10.1016/j.tetlet.2007.09.143
[15]. Andrade, C. K. Z.; Barreto, A. S.; Silva, W. A. Arkivoc 2008, 12, 226-232.
[16]. Al-Mousawi, S. M.; El-Apasery, M. A.; Elnagdi, M. H. Molecules 2010, 15, 58-67.
doi:10.3390/molecules15010058
PMid:20110871
[17]. Al-Saleh, B.; El-Apasery, M. A.; Abdel-Aziz, R. S.; Elnagdi, M. H. J. Heterocycl. Chem. 2005, 42(4), 563-566.
doi:10.1002/jhet.5570420414
[18]. El-Dusouqui, O. M. E.; Abdelkhalik, M. M.; Al-Awadi, N. A.; Dib, H. H.; George, B. J.; Elnagdi, M. H. J. Chem. Res. 2006, 5, 295-302.
[19]. Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Rosa, F. A.; Marzari, M. R. B.; Zanatta, N.; Bonacorso, H. G. Catalysis Commun. 2008, 9(6), 1375-1378.
doi:10.1016/j.catcom.2007.11.037
Supporting information
The Supplementary Material for this article can be found online at: Supplementary files
How to cite
El-Apasery, M.; Al-Mousawi, S.; Elnagdi, M.
Eur. J. Chem.
2011,
2(2), 168-172.
doi:10.5155/eurjchem.2.2.168-172.228
El-Apasery, M.; Al-Mousawi, S.; Elnagdi, M. Green methodologies in organic synthesis: Microwave assisted solvent- and catalyst-free synthesis of enaminones and their conversion into 1,3,5-trisubstituted benzenes as well as 3-aroyl-6-substituted pyridines.
Eur. J. Chem.
2011,
2(2), 168-172.
doi:10.5155/eurjchem.2.2.168-172.228
El-Apasery, M., Al-Mousawi, S., & Elnagdi, M.
(2011).
Green methodologies in organic synthesis: Microwave assisted solvent- and catalyst-free synthesis of enaminones and their conversion into 1,3,5-trisubstituted benzenes as well as 3-aroyl-6-substituted pyridines.
European Journal of Chemistry, 2(2), 168-172.
doi:10.5155/eurjchem.2.2.168-172.228
El-Apasery, Morsy, Saleh Mohamed Al-Mousawi, & Mohamed Helmy Elnagdi.
"Green methodologies in organic synthesis: Microwave assisted solvent- and catalyst-free synthesis of enaminones and their conversion into 1,3,5-trisubstituted benzenes as well as 3-aroyl-6-substituted pyridines." European Journal of Chemistry [Online], 2.2 (2011): 168-172. Web. 22 Jan. 2020
El-Apasery, Morsy, Al-Mousawi, Saleh, AND Elnagdi, Mohamed.
"Green methodologies in organic synthesis: Microwave assisted solvent- and catalyst-free synthesis of enaminones and their conversion into 1,3,5-trisubstituted benzenes as well as 3-aroyl-6-substituted pyridines" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)
DOI Link: https://doi.org/10.5155/eurjchem.2.2.168-172.228
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
European Journal of Chemistry 2011, 2(2), 168-172 | doi: https://doi.org/10.5155/eurjchem.2.2.168-172.228 | Get rights and content
Refbacks
- There are currently no refbacks.
Copyright (c)
© 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.