Expedient and Diastereoselective Synthesis of Substituted 6,6a-Dihydroisoindolo[2,1-a]quinolin-11(5H)-ones
| Autor: | Amitabh Jha, Zainab Al-Jaroudi, Prabhu P. Mohapatra, T. Stanley Cameron |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Ketone 010405 organic chemistry Aryl Organic Chemistry Intramolecular cyclization Electrophilic aromatic substitution 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Anhydrous Organic chemistry Lewis acids and bases Alkyl |
| Zdroj: | Synthesis. 48:4477-4488 |
| ISSN: | 1437-210X 0039-7881 |
| Popis: | Further synthetic utility of 3-substituted N-arylisoindolinones obtained from N-aryl-3-hydroxyisoindolinones and alkyl aryl ketones under Lewis acid mediated anhydrous conditions is reported. Herein, substituted 6,6a-dihydroisoindolo[2,1-a]quinolin-11(5H)-ones were synthesized from 3-substituted isoindolinones following a NaBH4 ketone reduction and carbocation-mediated intramolecular electrophilic aromatic substitution using BF3·OEt2. Representative final products were unambiguously characterized by single-crystal X-ray crystallography. |
| Databáze: | OpenAIRE |
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