Cargando…
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...
Autores principales: | , , , , , , |
---|---|
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 |
_version_ | 1782303765520449536 |
---|---|
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. |
format | Online Article Text |
id | pubmed-3924718 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | BioMed Central |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT barakatassem tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives AT almajidabdullahmohammed tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives AT alghamdiabdulazizmoshabab tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives AT mabkhotyahianasser tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives AT rafiqhussainsiddiquimohammed tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives AT ghabbourhazema tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives AT funhoongkun tandemaldolmichaelreactionsinaqueousdiethylaminemediumagreenerandefficientapproachtodimedonebarbituricacidderivatives |