Acylacetylenes in multiple functionalization of hydroxyquinolines and quinolones. Issue 43 (23rd October 2020)

• Record Type: Journal Article
• Authors: Belyaeva, Kseniya V.; Nikitina, Lina P.; Afonin, Andrei V.; Trofimov, Boris A.
• Is Part Of: Tetrahedron. Volume 76:Issue 43(2020)
• Publication Date: 2020-10-23
• Subjects: Alkynes -- Enones -- Functionalization -- Nucleophilic addition -- Regioselectivity -- Quinolines -- Quinolones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131523
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The expected one-pot multiple functionalization of hydroxyquinolines and quinolones with acylacetylenes (20 mol% KOH, 5 equiv. H2 O, MeCN, 55–60 °C), which, according to the previous finding, might involve the addition of OH and NH-functions to the triple bond and insertion of acylacetylenes into the quinoline scaffold, retains mainly on the formation of chalcone-quinoline ensembles in up 99% yield. The higher functionalized quinolines can be obtained in a synthetically acceptable yield, when the above ensembles are treated with the second molecule of acylacetylenes. Thus, the further insertion of second molecule of the acetylenes into the quinoline scaffold occurs as a much slower process indicating a strong adverse substituent effect of the remote chalcone moiety. Graphical abstract: Image 1 Highlights: C -, O -, or N -functionalizations of quinoline core. Broad scope, short reaction time. Excellent product yields.