Solvent-free mechanochemical conversion of 3-ethoxysalicylaldehyde and primary aromatic amines to corresponding Schiff-bases. Issue 1 (7th January 2015)

• Record Type: Journal Article
• Authors: Tigineh, Getinet Tamiru; Wen, Yuh-Sheng; Liu, Ling-Kang
• Is Part Of: Tetrahedron. Volume 71:Issue 1(2015)
• Page Start: 170
• Page End: 175
• Publication Date: 2015-01-07
• Subjects: Mechanochemistry -- Primary aromatic amine -- Schiff-base -- Solvent-free reaction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2014.10.074
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Mechanochemical processes are both solvent-free and less energy consuming than standard solution reactions and are rapidly becoming popular as green and sustainable alternative to conventional solution-based processes. In this paper, fifteen Schiff-bases of differently functionalized solid primary aromatic amines were successfully synthesized using 1:1 molar ratio of 3-ethoxysalicylaldehyde to solid amine, by co-grinding in mortar with a pestle for 2–10 min under solvent-free environment at room temperature. Nine of fifteen were synthesized for the first time and the Schiff-bases were investigated by analytical and spectroscopic techniques. The excellent conversion to products, with virtually zero work-up, and isolation of species, which cannot be obtained in solution, make the mechanochemical approach a worthwhile click and green method for Schiff-base synthesis. Graphical abstract: