2012
DOI: 10.1080/00397911.2011.593106
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Facile Microwave-Assisted Michael Addition of Diphenacyl Sulfides to Chalcones Under Solvent-Free Conditions: Generation of Symmetrical and Unsymmetrical 1,5-Diketones

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Cited by 11 publications
(7 citation statements)
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“…Current literature describes the Michael reaction as an efficient method of formation carbon-carbon bond leading to 1,5-diketones. Nowadays, there are many possibilities to obtain 1,3,5-triarylpentan-1,5-dione derivatives from chalcones and enolates using e.g., trimethyl orthoformate, triflic acid and carbon tetrachloride as a solvent [31], various barium alkoxides [32], sodium sulfide [33] or using microwave irradiation [34], which are not as environmentally friendly as biotransformations. To our knowledge, there are no prior studies to obtain 1,3,5-triarylpentan-1,5-diones as a result of microbial transformation, without such harmful and toxic reagents.…”
Section: Biotransformation Of 4-hydroxy-4 -Methylchalcone (4)mentioning
confidence: 99%
“…Current literature describes the Michael reaction as an efficient method of formation carbon-carbon bond leading to 1,5-diketones. Nowadays, there are many possibilities to obtain 1,3,5-triarylpentan-1,5-dione derivatives from chalcones and enolates using e.g., trimethyl orthoformate, triflic acid and carbon tetrachloride as a solvent [31], various barium alkoxides [32], sodium sulfide [33] or using microwave irradiation [34], which are not as environmentally friendly as biotransformations. To our knowledge, there are no prior studies to obtain 1,3,5-triarylpentan-1,5-diones as a result of microbial transformation, without such harmful and toxic reagents.…”
Section: Biotransformation Of 4-hydroxy-4 -Methylchalcone (4)mentioning
confidence: 99%
“…4 However, some of these methods use air-and moisture-sensitive materials and require manipulation using complex techniques; some of these methods use materials with unpleasant odors that oen cause environment pollution. In this work, a novel method for the synthesis of 1,3,5-triarylpentane-1,5-diones is reported using a,b-unsaturated ketones as the unique starting materials and inexpensive cuprous iodide as the catalyst (Scheme 2).…”
Section: Introductionmentioning
confidence: 99%
“…The reported synthetic methods for 1,3,5-triarylpentane-1,5diones (Scheme 1) include: (1) using benzaldehyde and acetophenone as the raw materials by Michael addition reaction; 2 (2) using a,b-unsaturated ketones (or benzaldehyde) and silyl enol ethers as the starting materials in the presence of magnesium chloride (or sodium hydroxide); 3 (3) using a,b-unsaturated ketones and diphenacyl suldes as the starting materials under microwave irradiation. 4 However, some of these methods use air-and moisture-sensitive materials and require manipulation using complex techniques; some of these methods use materials with unpleasant odors that oen cause environment pollution. In this work, a novel method for the synthesis of 1,3,5-triarylpentane-1,5-diones is reported using a,b-unsaturated ketones as the unique starting materials and inexpensive cuprous iodide as the catalyst (Scheme 2).…”
Section: Introductionmentioning
confidence: 99%
“…These heterocycles have important applications in modern drug design and in the chemistry of functional materials . Consequently, much effort has been devoted to the chemical synthesis of 1,5-diketones. ,, The most common classical methods of 1,5-diones synthesis are (i) Claisen–Schmidt condensation following Michael addition reaction of aryl methyl ketones and benzaldehyde derivatives under a basic condition and using silica vanadic acid as a heterogeneous catalyst (Scheme a), (ii) catalyzed Michael reactions of chalcones (α,β-unsaturated ketones) with aryl methyl ketones, silyl enol ethers, , and diphenacyl sulfides (Scheme b), (iii) from α,β-unsaturated ketones via base-induced retro-aldol and Michael addition using copper and cobalt as catalysts, , (Scheme c), (iv) via nickel on silica-alumina-catalyzed direct α-alkylation of aryl methyl ketones with benzyl alcohol (Scheme d), and (v) silver- and rhodium-catalyzed reactions of aromatic and aliphatic aldehydes with cyclopropanol and cyclobutanol derivatives. , However, these synthetic methods use expensive catalysts and additives, toxic organic solvents, and air- and moisture-sensitive materials. Additionally, the yields of 1,5-diketones through these reactions were low either due to by-product formation such as aromatic aldehydes , or no product formation at all under base-mediated condensation .…”
Section: Introductionmentioning
confidence: 99%