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Catalyst- and solvent-free Csp2–H functionalization of 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling under ball-milling.
- Source :
- Green Chemistry; 7/7/2021, Vol. 23 Issue 13, p4762-4770, 9p
- Publication Year :
- 2021
-
Abstract
- A one-pot procedure for the synthesis of biologically relevant coumarin hydrazones using a three-component reaction between 4-hydrocoumarins, primary aromatic amines and tert-butyl nitrite under ball-milling in the absence of any catalysts/additives and solvents has been developed. The mechanical force implements the C<subscript>sp<superscript>2</superscript></subscript>–H functionalization of 4-hydroxycoumarins via C-3 dehydrogenative aza-coupling with ease. The product was isolated by simple washing of the crude reaction residue with aqueous ethanol, followed by simple filtration. No chromatographic purification was required. Catalyst- and solvent-free reaction conditions, use of ball-milling as a green tool, lack of a need for chromatographic purification, broad substrate scope and tolerance for various functional groups, high yields of products at short reaction times (no more than 6 min), a clean reaction profile, and gram-scale synthetic applicability make this procedure green and cost-effective. [ABSTRACT FROM AUTHOR]
- Subjects :
- AROMATIC amines
COUMARINS
FUNCTIONAL groups
HYDRAZONES
NITRITES
SOLVENTS
CATALYSTS
Subjects
Details
- Language :
- English
- ISSN :
- 14639262
- Volume :
- 23
- Issue :
- 13
- Database :
- Complementary Index
- Journal :
- Green Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 151249094
- Full Text :
- https://doi.org/10.1039/d1gc01341f