Solvent‐Free Ball‐Milling Biginelli Reaction by Subcomponent Synthesis. Issue 32 (8th October 2015)

• Record Type: Journal Article
• Authors: Sahoo, Prasit Kumar; Bose, Anima; Mal, Prasenjit
• Is Part Of: European journal of organic chemistry. Issue 32(2015)
• Page Start: 6994
• Page End: 6998
• Publication Date: 2015-10-08
• Subjects: Synthetic methods -- Multicomponent reactions -- Mechanochemistry -- ­Biginelli reaction -- Ball mill; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201501039
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: We report here an understanding of systems chemistry on small molecules through covalent mechanochemistry. As a proof‐of‐concept, the multicomponent Biginelli reaction by subcomponent synthesis was considered as a model system. Reactions were performed under solvent‐free, metal‐free, mechanochemical (ball milling) and ambient laboratory conditions. Br + ‐catalyzed oxidation of benzyl alcohols led to the product benzaldehydes and byproduct H + which were further promoted as component and catalyst, respectively, for a cascade transformation to dihydropyrimidones within the same reaction pot. Remarkably, in solution, the reaction system could not be reproduced at room temperature even after 24 h. Abstract : Under solvent‐free ball‐milling conditions, multicomponent Biginelli reactions for the synthesis of dihydropyrimidones were performed by subcomponent synthesis of reagents (aldehydes) and catalyst (H + ) from Br + oxidation of benzyl alcohols.