Highly Selective Synthesis of α-Hydroxy, α-Oxy, and α-Oxo Amides by a Post-Passerini Condensation Transformation
| Autor: | Farzaneh Bandehali-Naeini, Sima Karami, Zahra Gholami-Koupaei, Saeedeh Soheil-Moghaddam, Maryam-Sadat Tonekaboni, Delaram Ebrahimi, Behrouz Notash, Morteza Shiri |
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| Rok vydání: | 2021 |
| Předmět: |
cyclization
deacetylation post-condensation transformation iodine 010405 organic chemistry Organic Chemistry Condensation Aromatization Alcohol 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences Transformation (genetics) chemistry.chemical_compound Passerini adduct chemistry Cascade reaction Acetylation cascade reaction Methanol Solvolysis dealkynylation |
| DOI: | 10.6084/m9.figshare.14119796 |
| Popis: | A post-Passerini condensation transformation can be employed in the synthesis of three types of amides: α-hydroxy, α-oxy, and α-oxo amides. K2CO3 efficiently promotes the solvolysis of α-acetoxy amides to form α-hydroxy amides in methanol. 2-Acetoxy-2-(2-alkynylquinolin-3-yl)acetamides in basic methanol are cyclized to 1,3-dihydrofuro[3,4-b]quinoline-1-carboxamides via deacetylation and 5-exo-dig cyclization. Treatment of 2-hydroxy-2-[2-(phenylethynyl)quinolin-3-yl]acetamides with I2 in basic media produces pyrrolo[2,3-b]quinoline-2,3-diones. This cyclization involves intramolecular cyclization, dealkynylative aromatization, and oxidation of the secondary alcohol. |
| Databáze: | OpenAIRE |
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