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Selenocysteinyl electrophiles efficiently promote the formation of coumarin and quinolinone cores by 6-endo-dig cyclization.
- Source :
-
New Journal of Chemistry . 9/28/2021, Vol. 45 Issue 36, p16625-16634. 10p. - Publication Year :
- 2021
-
Abstract
- Efficient methods have been disclosed for the construction of nitrogen and oxygen containing heterocyclic systems attached to selenocysteine or selenoglutathione. An inorganic oxidant (K2S2O8) or a mild Lewis acid (CuBr2) was employed for the generation of selanyl electrophiles that were further trapped with phenyl propiolates, methyl 2-(phenylethynyl)benzoate, N-phenyl propiolamides and 2-(phenylethynyl)benzamide thus providing the respective coumarins, isocoumarins, quinolin-2-ones and isoquinolin-2-ones via 6-endo-dig cyclization. The use of visible light resulted in divergent reactivity providing triple bond addition products or spirocyclic compounds bearing selenocysteine moieties. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 45
- Issue :
- 36
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 152553296
- Full Text :
- https://doi.org/10.1039/d1nj02633j