Tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester in water: an efficient and sustainable synthesis of 1,3,4′-tricarbonyl compounds

Fan, Xuesen; He, Yan; Cui, Liangyan; Zhang, Xinying; Wang, Jianji

doi:10.1039/c1gc15707h

Cited by 27 publications

(10 citation statements)

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“…Our study found that allenic ketone 1 could be deprotonated by TBAF·3H 2 O to afford an anion intermediate 74 , which then underwent a nucleophilic substitution with 14 to give 75 . The allenyl moiety in 75 was then hydrolyzed under the promotion of TBAF·3H 2 O to yield 1,3,4'‐triketone 76 (Scheme ) 31…”

Section: Reactions Of 12‐allenic Ketonesmentioning

confidence: 99%

Recent Advances in the Reactions of 1,2-Allenic Ketones and α-Allenic Alcohols

Fan

Zhang

2016

The Chemical Record

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This Personal Account summarizes our recent efforts in searching for novel synthetic strategies for a number of organic molecules by using allene derivatives as valuable substrates. It starts with a concise description of the background of allene-related synthetic chemistry. The second part deals with the reactions of 1,2-allenic ketones, including the reactions of 1,2-allenic ketones with various nucleophiles to afford functionalized benzenes, heterocycles, and fluoroenones, and those of allenic ketones as nucleophiles under the promotion of bases to provide 1,3,4'-triones or functionalized furans. The third part of this account focuses on the reactions of α-allenic alcohols. In this section, multicomponent reactions involving α-allenic alcohols, and cascade reactions of α-allenic alcohols promoted by Brønsted acid or iodine, are presented.

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Section: Reactions Of 12‐allenic Ketonesmentioning

confidence: 99%

Recent Advances in the Reactions of 1,2-Allenic Ketones and α-Allenic Alcohols

Fan

Zhang

2016

The Chemical Record

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“…[40][41][42] In this paper, we report the regioselective perpetration of pyrazoles by condensation of hydrazines/hydrazides with various compounds including 1,3-diketones and b-ketoesters, via the Knorr synthesis using CSA as an efficient, reusable, and environmentally friendly heterogeneous acidic catalyst at room temperature in pure water. 13 CNMR spectra were recorded on a Bruker Avance DPX-62.5 MHz spectrometer (CDCl 3 or DMSO solution). The IR spectra were run on a Perkin Elmer 780 spectrophotometer in KBr pellets and reported in cm À1 .…”

Section: Introductionmentioning

confidence: 99%

“…In addition, water as a solvent will reduce the use of harmful organic solvents and may lead to the development of environmentally-friendly chemical processes. [7][8][9][10][11][12][13][14][15] Therefore, water as a reaction medium would be highly desirable if such reactions could be performed using reusable catalysts.…”

Section: Introductionmentioning

confidence: 99%

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Cellulose sulfuric acid as a bio-supported and efficient solid acid catalyst for synthesis of pyrazoles in aqueous medium

2014

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A convenient and practical method was described for the regioselective synthesis of pyrazoles from hydrazines/hydrazides and 1,3-dicarbonyl compounds via the Knorr synthesis in water with cellulose sulfuric acid (CSA) as a biopolymer-based solid acid catalyst. Various hydrazines and hydrazides were reacted with 1,3 diketones and the desired pyrazoles were obtained in high yields. The reaction of less reactive hydrazines with 1,3-dicarbonyl compounds stopped at the corresponding hydrazone derivatives.Hydrazides were employed with b-ketoester, and imine adducts were the only isolated product. Simple isolation of products, mild reaction conditions, reusability of solid acid catalysts and short reaction times are advantages of this green procedure.

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“… When this set of diketones were treated with p TSA in toluene, the 3-phosphorylated furans 7a – 7f were obtained in 71–88% yields (Scheme ). Upon subjecting 3a , 3d , and 3g with Lawesson’s reagent in toluene at 70 °C, 3-phosphorylated thiophenes 8a – 8c were obtained in 81–88% yields (Scheme ). Finally, these diketones could be converted to 4-phosphorylated 2,5-dihydropyridazines 9a – 9c using PhNHNH 2 in excellent yields of 93–98% (Scheme ).…”

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Global Access to 3/4-Phosphorylated Heterocycles via a Carbene-Catalyzed Stetter Reaction of Vinylphosphonates and Aldehydes

et al. 2020

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The first global method for the preparation of 3phosphorylated-pyrroles, -furans, -thiophenes, and 4-phosphorylated 2,5-dihydropyridazines is reported. To achieve this, the first protocol for the direct synthesis of α-phosphorylated 1,4-diketones has been developed through a carbene-catalyzed Stetter reaction of vinylphosphonates and aldehydes. This is the first synthetic method for accessing 4-phosphorylated 2,5-dihydropyridazines. This process is metal-free and produces multifunctionalized heterocycles.

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Tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester in water: an efficient and sustainable synthesis of 1,3,4′-tricarbonyl compounds

Cited by 27 publications

References 50 publications

Recent Advances in the Reactions of 1,2-Allenic Ketones and α-Allenic Alcohols

Recent Advances in the Reactions of 1,2-Allenic Ketones and α-Allenic Alcohols

Cellulose sulfuric acid as a bio-supported and efficient solid acid catalyst for synthesis of pyrazoles in aqueous medium

Global Access to 3/4-Phosphorylated Heterocycles via a Carbene-Catalyzed Stetter Reaction of Vinylphosphonates and Aldehydes

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