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• W4200424552 endingPage "112021" @default.
• W4200424552 startingPage "112021" @default.
• W4200424552 abstract "• Oxidation – Knoevenagel condensation – Michael addition three-step cascade. • 2-Amino-chromene derivative synthesized from commodity chemicals. • Delayed addition of reagents results in faster kinetics and higher chromene yields. • Sequential addition grants 10-fold faster reactions in Knoevenagel condensations. • Co-condensation and thiol-ene addition allow for catalyst bifunctionality. A key challenge is design of materials and processes whereby competing reagents or conditions do not harm the multi-step sequence, thus allowing for more efficient chemical synthesis with elimination of work-up and separation steps. In this work, a three-step reaction cascade is performed using a porous bifunctional dimethylpropylamine-TEMPO-MCM41 catalyst, converting the commodity chemicals benzyl alcohol, sodium hypochlorite, and malononitrile to a biologically active anti-cancer, and anti-malarial 2-amino-chromene derivative. The cascade first utilizes a TEMPO-catalyzed oxidation of benzyl alcohol to benzaldehyde with NaOCl as the terminal oxidant. This is followed by a two-step, dual base catalyzed Knoevenagel condensation with malononitrile followed by a Michael addition with lawsone. Optimal conditions converting benzyl alcohol to 2-amino-5,10-dioxo-4-phenyl-5,10-dihydro-4H-benzo[g]chromene-3-carbonitrile include the delayed addition of malononitrile and lawsone during the three-step reaction sequence, which results in a 2-amino-chromene yield of over 80%. The importance of stepwise reagent addition is rationalized due to the unfavorable adsorption of acidic lawsone on the surface-grafted base catalyst. Tertiary Brønsted base sites of dimethylpropylamine outperform the more Lewis basic primary propylamine functionalized catalyst. This work outlines a simple and effective method for generating mesoporous materials with two types of active sites via co-condensation and thiol-ene coupling procedures." @default.
• W4200424552 created "2021-12-31" @default.
• W4200424552 creator A5052807182 @default.
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• W4200424552 creator A5081848414 @default.
• W4200424552 date "2022-01-01" @default.
• W4200424552 modified "2023-10-17" @default.
• W4200424552 title "Design of a bifunctional TEMPO-tertiary amine mesoporous silica catalyst for the three-step cascade synthesis of a chromene derivative" @default.
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• W4200424552 doi "https://doi.org/10.1016/j.mcat.2021.112021" @default.
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