Multicomponent Synthesis of 4-Aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines Using L-Proline as a Catalyst—Does It Really Proceed?

• Published in: Molecules (Basel, Switzerland) Switzerland), 2023-11, Vol.28 (22), p.7612
• Main Authors: Danel, Andrzej, Porębska, Elżbieta, Markiel, Kacper, Havrysh, Oleksii, Kucharek, Mateusz, Gut, Arkadiusz, Uchacz, Tomasz
• Format: Article
• Language: English
• Subjects: 4,4-(phenyl-methylene)-bis-(3-methyl-1-phenylpyrazol-5-oles); 4-aryl-4,9H-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline; Aldehydes; L-proline; multi-component reactions; Nitrogen
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28227612

Looking for effective synthetic methods for 1H-pyrazolo[3,4-b]quinolines preparation, we came across a procedure where, in a three-component reaction catalysed by L-proline, 4-aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines are formed. These compounds can be easily oxidised to a fully aromatic system, which gives hope for a synthetic method that could replace, e.g., Friedländer condensation, often used for this purpose, even though severely limited by the availability of suitable substrates. However, after careful repetition of the procedures described in the publication, it turned out that the compounds described therein do not form at all. The actual compounds turned out to be 4,4-(phenyl-methylene)-bis-(3-methyl-1-phenylpyrazol-5-oles). Therefore, 4-Aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines were prepared by another method and used as standards to compare the products formed in the original procedure.