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
| Autor: | Ashiq Hussain Padder, H. Surya Prakash Rao |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Nitrile 010405 organic chemistry General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Organic molecules chemistry.chemical_compound chemistry Materials Chemistry Blaise reaction Reactivity (chemistry) Alkyl |
| Zdroj: | New Journal of Chemistry. 44:9010-9017 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/d0nj00231c |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|