Cyanoquinolines and Furo[3,4-b]quinolinones Formation via On-The-Spot 2,3-Functionalization of Quinolines with Cyanopropargylic Alcohols.

A convenient approach to 2-(1-ethoxyalkoxy)-3-cyanoquinolines (in up to 50% yields) has been developed. The approach comprises functionalization of quinolines with acetals of cyanopropargylic alcohols (KOH/H2O/MeCN, 55-60 °C) followed by their transformation to furo[3,4-b]quinolinones (in up to 98% yields) via the sequential removal of acetal protection and intramolecular cyclization/hydration (7% aqueous HCl, acetone, 20-25 °C).

Citation

Kseniya V Belyaeva, Lina P Nikitina, Andrey V Afonin, Ludmila A Grishchenko, Boris A Trofimov. Cyanoquinolines and Furo[3,4-b]quinolinones Formation via On-The-Spot 2,3-Functionalization of Quinolines with Cyanopropargylic Alcohols. The Journal of organic chemistry. 2021 Mar 05;86(5):3800-3809

PMID: 33605731

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