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Abstract

A microwave-assisted, continuous-flow organic synthesis (MACOS) protocol for the synthesis of functionalized 1,2,5-thiadiazepane 1,1-dioxide library, utilizing a one-pot elimination and inter-/intramolecular double aza-Michael addition strategy is reported. The optimized protocol in MACOS was utilized for scale-out and further extended for library production using a multicapillary flow reactor. A 50-member library of 1,2,5-thiadiazepane 1,1-dioxides was prepared on a 100- to 300-mg scale with overall yields between 50 and 80% and over 90 % purity determined by proton nuclear magnetic resonance (1H-NMR) spectroscopy.

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Abstract

We have successfully demonstrated that a microflow reactor is extremely useful in controlling reactions involving an unstable o-benzoquinone. As a model reaction, Michael addition reaction between o-benzoquinone generated from electrochemical oxidation of catechol and benzenethiols was employed. This reaction system enables selective oxidation of catechol avoiding the oxidation of benzenethiol, although these oxidation potentials are close to each other. The examination of several reaction conditions indicated that the key features of the method are an effective o-benzoquinone generation and its rapid use for the following reaction without decomposition in a microflow system. In addition, cyclic voltammetry measurements elucidated that catechol concentration and selection of anode material were crucial factors for effective o-quinone generation.

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Journal of Flow Chemistry
Authors: Laura Carroccia, Biagia Musio, Leonardo Degennaro, Giuseppe Romanazzi, and Renzo Luisi

Abstract

Microreactor-mediated organocatalysed Michael reactions have been developed. By using a soluble proline-derived catalyst, Michael-type reactions, leading to γ-nitroketones, have been optimized in homogeneous and continuous-flow conditions. As proof of principle, an integrated microfluidic system able to perform domino processes useful in the preparation of bicyclo[4.4.0]decanes with six contiguous stereogenic centres has been set up.

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Tertiary-Amine Catalyzed Michael Addition of Multifunctional Thiols to Multifunctional Acrylates ” C. O. Bounds , J. Upadhyay , N. Totaro , S. Thakuri , L. Garber , M. Vincent , Z. Huang , M. Hupert , J. A. Pojman * ACS Applied Materials

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]. It is well known that typical solid bases, i.e., alkali-earth metal oxides, promote the isomerization of 1-butene, hydrogenation of 1,3-butadiene, aldol condensation of acetone, and Michael addition of methyl crotonate [ 1 ]. Although many

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(oxidation, olefination, Michael addition, hydrogenation, and saponification). The methodology starts with two sequential modules that are necessary for the synthesis of all product classes from alcohol starting materials: oxidation to the corresponding

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. A. de Souza * Organic & Biomolecular Chemistry 2013 , 11 , 6806 – 6813 . “Continuous flow, highly enantioselective Michael additions catalyzed by a PS-supported squaramide” P. Kasaplar , C. Rodriguez-Escrich , M. A

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subsequent intramolecular Michael addition of benzaldehyde and 2-hydroxyacetonphenone to flavanone at 140 °C under solvent-free conditions, and the results are outlined in Table 3 . Aminopropyl-functionalized silica-E displays a higher conversion of 2

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Synthesis of PAN4 Acrylonitrile-capped poly(propylene imine) dendrimer was synthesized via the single-molecule Michael addition between primary amine functionalities and double bonds of acrylonitrile under ambient conditions to afford an amine

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