DMSO as a Methine Source in TFA-Mediated One-Pot Tandem Regioselective Synthesis of 3‑Substituted-1-Aryl‑1H‑Pyrazolo-[3,4‑b]quinolines from Anilines and Pyrazolones

An acid-mediated and DMSO participant one-pot tandem synthesis of 3-substituted-1-aryl-1H-pyrazolo-[3,4- b]­quinoline from readily available anilines and pyrazolones was achieved. This method enables regioselective construction of the valuable heterocycles under transition-metal and oxidant-free con...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-02, Vol.86 (3), p.2658-2666
Main Authors: Yadav, Pushpendra, Awasthi, Annapurna, Gokulnath, Sabapathi, Tiwari, Dharmendra Kumar
Format: Article
Language:English
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Summary:An acid-mediated and DMSO participant one-pot tandem synthesis of 3-substituted-1-aryl-1H-pyrazolo-[3,4- b]­quinoline from readily available anilines and pyrazolones was achieved. This method enables regioselective construction of the valuable heterocycles under transition-metal and oxidant-free conditions in which DMSO acts as a methine source as well as solvent making this process an environmentally benign approach. A broad range of diversely substituted aryl amines and pyrazolines are successfully employed in this reaction to access a series of pyrazolo­[4,3-c]­quinolones through a novel cascade mechanism. Furthermore, the application and mechanistic studies of the present methodology also demonstrated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c02696