Transition-Metal-Free Cascade Synthesis of 4-Quinolones: Umpolung of Michael Acceptors via Ene Reaction with Arynes
| Autor: | Hengyao You, Chandraiah Lagishetti, R. Santhosh Reddy, I. N. Chaithanya Kiran, Yun He |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Ketone 010405 organic chemistry Chemistry Organic Chemistry Substrate (chemistry) 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Aryne 0104 chemical sciences Catalysis Adduct Umpolung Organic chemistry Reactivity (chemistry) Physical and Theoretical Chemistry Ene reaction |
| Zdroj: | Organic Letters. 18:3818-3821 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.6b01830 |
| Popis: | A novel "one-pot" aryne transformation is described that affords various 4-quinolone derivatives without recourse to transition-metal catalysis. Arynes react with aza-Morita-Baylis-Hillman (AMBH) adducts through a cascade sequence involving an insertion/cyclization/ene reaction process to afford 4-quinolones in high yields with a broad substrate scope under mild reaction conditions. Essentially, an umpolung of reactivity at the β carbon of α,β-unsaturated ketone has been achieved by an inverse electron demand aryne-ene reaction to provide a C-arylated product. |
| Databáze: | OpenAIRE |
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