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Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives

BACKGROUND: Green chemistry is a rapidly developing new field that provides us with a proactive avenue for the sustainable development of future science and technologies. Green chemistry uses highly efficient and environmentally benign synthetic protocols to deliver lifesaving medicines, acceleratin...

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Autores principales: Barakat, Assem, Al-Majid, Abdullah Mohammed, Al-Ghamdi, Abdulaziz Moshabab, Mabkhot, Yahia Nasser, Rafiq Hussain Siddiqui, Mohammed, Ghabbour, Hazem A, Fun, Hoong-Kun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3924718/
https://www.ncbi.nlm.nih.gov/pubmed/24485059
http://dx.doi.org/10.1186/1752-153X-8-9
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author Barakat, Assem
Al-Majid, Abdullah Mohammed
Al-Ghamdi, Abdulaziz Moshabab
Mabkhot, Yahia Nasser
Rafiq Hussain Siddiqui, Mohammed
Ghabbour, Hazem A
Fun, Hoong-Kun
author_facet Barakat, Assem
Al-Majid, Abdullah Mohammed
Al-Ghamdi, Abdulaziz Moshabab
Mabkhot, Yahia Nasser
Rafiq Hussain Siddiqui, Mohammed
Ghabbour, Hazem A
Fun, Hoong-Kun
author_sort Barakat, Assem
collection PubMed
description BACKGROUND: Green chemistry is a rapidly developing new field that provides us with a proactive avenue for the sustainable development of future science and technologies. Green chemistry uses highly efficient and environmentally benign synthetic protocols to deliver lifesaving medicines, accelerating lead optimization processes in drug discovery, with reduced unnecessary environmental impact. From this view point, it is desirable to use water instead of organic solvents as a reaction medium, since water is safe, abundant and an environmentally benign solvent. RESULTS: A convenient one-pot method for the efficient synthesis of the novel Zwitterion derivatives 4a-pvia a three-component condensation reaction of barbituric acid derivatives 1a,b, dimedone 2, and various aldehydes 3 in the presence of aqueous diethylamine media is described. This new approach is environmentally benign, with clean synthetic procedure, short reaction times and easy work-up procedure which proceeded smoothly to provide excellent yield (88-98%). The synthesized products were characterized by elemental analysis, IR, MS, NMR and CHN analysis. The structure of 4a was further confirmed by single crystal X-ray diffraction. The compound crystallizes in the orthorhombic space group Pbca with α = 14.6669 (5) Å, b = 18.3084 (6) Å, c = 19.0294 (6) Å, α = 90°, β = 90°, = 90°, V = 5109.9 (3) Å(3), and Z = 8. The molecules are packed in crystal structure by weak intermolecular C–H⋅ ⋅ ⋅O hydrogen bonding interactions. CONCLUSIONS: An environmentally benign Aldol-Michael protocol for the synthesis of dimedone-barbituric derivatives using aqueous diethylamine medium is achieved.
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spelling pubmed-39247182014-02-15 Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives Barakat, Assem Al-Majid, Abdullah Mohammed Al-Ghamdi, Abdulaziz Moshabab Mabkhot, Yahia Nasser Rafiq Hussain Siddiqui, Mohammed Ghabbour, Hazem A Fun, Hoong-Kun Chem Cent J Research Article BACKGROUND: Green chemistry is a rapidly developing new field that provides us with a proactive avenue for the sustainable development of future science and technologies. Green chemistry uses highly efficient and environmentally benign synthetic protocols to deliver lifesaving medicines, accelerating lead optimization processes in drug discovery, with reduced unnecessary environmental impact. From this view point, it is desirable to use water instead of organic solvents as a reaction medium, since water is safe, abundant and an environmentally benign solvent. RESULTS: A convenient one-pot method for the efficient synthesis of the novel Zwitterion derivatives 4a-pvia a three-component condensation reaction of barbituric acid derivatives 1a,b, dimedone 2, and various aldehydes 3 in the presence of aqueous diethylamine media is described. This new approach is environmentally benign, with clean synthetic procedure, short reaction times and easy work-up procedure which proceeded smoothly to provide excellent yield (88-98%). The synthesized products were characterized by elemental analysis, IR, MS, NMR and CHN analysis. The structure of 4a was further confirmed by single crystal X-ray diffraction. The compound crystallizes in the orthorhombic space group Pbca with α = 14.6669 (5) Å, b = 18.3084 (6) Å, c = 19.0294 (6) Å, α = 90°, β = 90°, = 90°, V = 5109.9 (3) Å(3), and Z = 8. The molecules are packed in crystal structure by weak intermolecular C–H⋅ ⋅ ⋅O hydrogen bonding interactions. CONCLUSIONS: An environmentally benign Aldol-Michael protocol for the synthesis of dimedone-barbituric derivatives using aqueous diethylamine medium is achieved. BioMed Central 2014-02-01 /pmc/articles/PMC3924718/ /pubmed/24485059 http://dx.doi.org/10.1186/1752-153X-8-9 Text en Copyright © 2014 Barakat et al.; licensee Chemistry Central Ltd. http://creativecommons.org/licenses/by/2.0 This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
Barakat, Assem
Al-Majid, Abdullah Mohammed
Al-Ghamdi, Abdulaziz Moshabab
Mabkhot, Yahia Nasser
Rafiq Hussain Siddiqui, Mohammed
Ghabbour, Hazem A
Fun, Hoong-Kun
Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
title Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
title_full Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
title_fullStr Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
title_full_unstemmed Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
title_short Tandem Aldol-Michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
title_sort tandem aldol-michael reactions in aqueous diethylamine medium: a greener and efficient approach to dimedone-barbituric acid derivatives
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3924718/
https://www.ncbi.nlm.nih.gov/pubmed/24485059
http://dx.doi.org/10.1186/1752-153X-8-9
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