2002
DOI: 10.1021/cc010043r
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Rapid Parallel Synthesis of Polymer-Bound Enones Utilizing Microwave-Assisted Solid-Phase Chemistry

Abstract: A microwave-assisted parallel solid-phase synthesis of a collection of 21 polymer-bound enones has been developed. The two-step protocol involves initial high-speed acetoacetylation of polystyrene Wang resin with a selection of seven common beta-ketoesters. When microwave flash heating at 170 degreesC was employed, complete conversions were achieved within 1-10 min, a significant improvement over the conventional thermal method, which takes several hours for completion. Significant rate enhancements were also … Show more

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Cited by 85 publications
(53 citation statements)
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“…[221] This approach required the synthesis of the 4-chloroacetoacetate resin as the key starting material, which was prepared by microwave-assisted acetoacetylation of hydroxymethyl polystyrene resin. In analogy to earlier work, [222] this transesterification was best carried out under open-vessel conditions in 1,2-dichlorobenzene (170 8C) to allow the formed methanol to be removed from the equilibrium (see also Scheme 20). This resin precursor was subsequently treated with urea and various aldehydes in an acid-catalyzed Biginelli multicomponent reaction (dioxane, 70 8C) to afford the corresponding resin-bound dihydropyrimidinones.…”
Section: Methodsmentioning
confidence: 99%
“…[221] This approach required the synthesis of the 4-chloroacetoacetate resin as the key starting material, which was prepared by microwave-assisted acetoacetylation of hydroxymethyl polystyrene resin. In analogy to earlier work, [222] this transesterification was best carried out under open-vessel conditions in 1,2-dichlorobenzene (170 8C) to allow the formed methanol to be removed from the equilibrium (see also Scheme 20). This resin precursor was subsequently treated with urea and various aldehydes in an acid-catalyzed Biginelli multicomponent reaction (dioxane, 70 8C) to afford the corresponding resin-bound dihydropyrimidinones.…”
Section: Methodsmentioning
confidence: 99%
“…As dielectric heating is a bulk technique, it is faster than heating based on conduction. Moreover, yet unexplained and surprisingly high catalytic reaction rates have been reported [10][11][12][13][14][15][16]. The present objective is to assess the feasibility of using a microwave sensitive catalytic material as a soot filter coating.…”
Section: Introductionmentioning
confidence: 99%
“…The first report on application of dedicated parallel microwave reactors for SPOS has been given by Strohmeier and Kappe (2002). In this report, they have carried out the microwave assisted synthesis of Knoevenagel products with the use of resin-bound β-ketoesters.…”
Section: Parallel Processing In Microwave Reactorsmentioning
confidence: 99%