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Oxidant-free, three-component synthesis of 7-amino-6 H -benzo[ c ]chromen-6-ones under green conditions.
- Source :
-
RSC advances [RSC Adv] 2019 Oct 16; Vol. 9 (57), pp. 32946-32953. Date of Electronic Publication: 2019 Oct 16 (Print Publication: 2019). - Publication Year :
- 2019
-
Abstract
- An oxidant-free three-component synthesis of biologically significant 7-amino-6 H -benzo[ c ]chromen-6-ones was established involving a Sc(OTf) <subscript>3</subscript> catalyzed three-component reaction between primary amines, β-ketoesters and 2-hydroxychalcones under green conditions. In this strategy, both the B and C rings of 6 H -benzo[ c ]chromen-6-ones were constructed simultaneously starting from acyclic precursors by generating four new bonds including two C-C, one C-N and one C-O in a single synthetic operation. The mechanism of this sequential cascade process involves the initial formation of a β-enaminone intermediate followed by Michael addition with 2-hydroxychalcone, intramolecular cyclization, dehydration, lactonization and aromatization steps. Unlike the related literature approaches, this reaction delivered the products without the addition of any external oxidants to achieve the key aromatization step.<br />Competing Interests: There are no conflicts to declare.<br /> (This journal is © The Royal Society of Chemistry.)
Details
- Language :
- English
- ISSN :
- 2046-2069
- Volume :
- 9
- Issue :
- 57
- Database :
- MEDLINE
- Journal :
- RSC advances
- Publication Type :
- Academic Journal
- Accession number :
- 35529159
- Full Text :
- https://doi.org/10.1039/c9ra07108c