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

Autor: Belyaeva KV; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation., Nikitina LP; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation., Afonin AV; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation., Grishchenko LA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation., Trofimov BA; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, Russian Federation.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Mar 05; Vol. 86 (5), pp. 3800-3809. Date of Electronic Publication: 2021 Feb 19.
DOI: 10.1021/acs.joc.0c02644
Abstrakt: 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/H 2 O/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).
Databáze: MEDLINE
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