Synthesis of quinolines and naphthyridines via catalytic retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes or nicotinaldehydes
| Autor: | Song-Lin Zhang, Zhu-Qin Deng |
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| Rok vydání: | 2016 |
| Předmět: |
Reaction conditions
010405 organic chemistry Aryl Organic Chemistry chemistry.chemical_element Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry Copper Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Aldol reaction Organic chemistry Physical and Theoretical Chemistry Selectivity Bond cleavage |
| Zdroj: | Organic & Biomolecular Chemistry. 14:8966-8970 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | A Cu(I)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα–Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields. |
| Databáze: | OpenAIRE |
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