Simple synthesis of 3-hydroxyquinolines via Na2S2O4-mediated reductive cyclization of (2-(2-nitrophenyl)oxiran-1-yl)(aryl)methanones (o-nitrobenzalacetophenone oxides)
| Autor: | Shamil K. Latypov, Dmitry E. Korshin, Ekaterina V. Mironova, Vera L. Mamedova, Gul'naz Z. Khikmatova, Il'dar Kh. Rizvanov, Olga B. Bazanova, Vakhid A. Mamedov, Victor V. Syakaev |
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| Rok vydání: | 2017 |
| Předmět: |
Reaction conditions
010405 organic chemistry Aryl Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences Sodium dithionite chemistry.chemical_compound chemistry Yield (chemistry) Intramolecular force Drug Discovery Functional group Organic chemistry Hydroxyquinolines |
| Zdroj: | Tetrahedron. 73:5082-5090 |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2017.06.058 |
| Popis: | An efficient sodium dithionite (Na2S2O4)-mediated method for construction of 3-hydroxyquinolines via in situ Meinwald rearrangement/intramolecular reductive cyclization of o-nitrobenzalacetophenone oxides has been developed. The practical approach is of excellent functional group compatibility with as high as 98% yield under mild reaction conditions. Moreover, further manipulation successfully furnished 4-bromo substituted derivatives which may provide a promising potential application in exploring biologically active analogs of 3-hydroxyquinolines. |
| Databáze: | OpenAIRE |
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