Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives
| Autor: | Emily B. Crull, Samer M. Beauti, Jared D. Hume, Amy H. Pham, Jacques J. Kessl, Nicholas G. Jentsch, Matthew Garrett Donahue, Julie A. Pigza |
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| Rok vydání: | 2018 |
| Předmět: |
Sodium
chemistry.chemical_element 010402 general chemistry 01 natural sciences Full Research Paper lcsh:QD241-441 chemistry.chemical_compound Residue (chemistry) lcsh:Organic chemistry quinoline Organic chemistry isatoic anhydride Carboxylate lcsh:Science HIV integrase masked acyl cyanide Triphosgene 010405 organic chemistry Quinoline Organic Chemistry 0104 chemical sciences Chemistry chemistry Sodium hydroxide Ethyl acetoacetate Electrophile cyclodehydration lcsh:Q |
| Zdroj: | Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry, Vol 14, Iss 1, Pp 2529-2536 (2018) |
| ISSN: | 1860-5397 |
| Popis: | A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation–build-up strategy of the ethyl ester at the 3-position allowed for the construction of the α-hydroxyacetic acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project. |
| Databáze: | OpenAIRE |
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