Stereoselective synthesis of (Z)-1,3-bis(α,β-unsaturated carbonyl)-isoindolines from aldehydes and phenacyl azides under metal free conditions
| Autor: | Jagadeesh Babu Nanubolu, Ahmed Kamal, Budaganaboyina Prasad, Mandalaparthi Phanindrudu, Dharmendra Kumar Tiwari |
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| Rok vydání: | 2021 |
| Předmět: |
Reaction conditions
Metals and Alloys General Chemistry Phenacyl Combinatorial chemistry Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound chemistry Cascade reaction Metal free Materials Chemistry Ceramics and Composites Stereoselectivity Piperidine |
| Zdroj: | Chemical Communications. 57:9542-9545 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/d1cc02884g |
| Popis: | Here in the present manuscript, we report our observation of an unprecedented stereoselective synthesis of 2H-isoindolin-1,3-ylidenes from 2-(formylphenyl)acrylates and phenacylazide in the presence of piperidine. Unlike in our previous findings, in which we accessed 3-keto-isoquinolines from the same starting materials under slightly modified reaction conditions, this unexpected one-pot tandem reaction allows an efficient and simple method to access a variety of highly functionalized ethyl (Z)-2-((Z)-3-(2-oxo-2-arylethylidene)-2,3-dihydro-1H-benzo[e]isoindol-1-ylidene)-acetates in very good to excellent yields (up to 91%). The present methodology is compatible with a wide variety of functional groups. |
| Databáze: | OpenAIRE |
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