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Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5H)-ones and the role of the strategically located ester on the reactivity of the nitriles.
- Source :
-
New Journal of Chemistry . 6/7/2020, Vol. 44 Issue 21, p9010-9017. 8p. - Publication Year :
- 2020
-
Abstract
- We have achieved a simple and convenient synthesis of several C(4) substituted 5-ylidenepyrrol-(5H)-ones from 3-aryl/heteroaryl/alkyl 3-cyanopropionates and ethyl/methyl bromoacetates via a useful variation of the classical Blaise reaction. The products were further transformed to useful small organic molecules (SOMs). Studies on the reactivity of nitriles via intra and inter-molecular competition experiments showed that anchimeric assistance from the neighbouring and strategically located ester is crucial for higher reactivity of the nitrile in the 3-cyanopropionates towards the Blaise reaction. [ABSTRACT FROM AUTHOR]
- Subjects :
- *SMALL molecules
*ESTERS
Subjects
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 44
- Issue :
- 21
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 143524535
- Full Text :
- https://doi.org/10.1039/d0nj00231c