Статья

Acylacetylenes in multiple functionalization of hydroxyquinolines and quinolones

K. Belyaeva, L. Nikitina, A. Afonin, B. Trofimov,
2021

The expected one-pot multiple functionalization of hydroxyquinolines and quinolones with acylacetylenes (20 mol% KOH, 5 equiv. H2O, 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. © 2020 Elsevier Ltd

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  • 1. Version of Record от 2021-04-27

Метаданные

Об авторах
  • K. Belyaeva
    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Sciences, 1 Favorsky Str., Irkutsk, 664033, Russian Federation
  • L. Nikitina
  • A. Afonin
  • B. Trofimov
Название журнала
  • Tetrahedron
Том
  • 76
Выпуск
  • 43
Страницы
  • -
Ключевые слова
  • 1 (2 furyl) 3 phenyl 3 (quinolin 3 yloxy)prop 2 en 1 one; 1 (2 furyl) 3 phenyl 3 (quinolin 4 yloxy)prop 2 en 1 one; 1 (2 furyl) 3 phenyl 3 (quinolin 6 yloxy)prop 2 en 1 one; 1 (2 furyl) 3 phenyl 3 (quinolin 8 yloxy)prop 2 en 1 one; 1 (3 methoxyphenyl) 3 phenyl 3 (quinolin 6 yloxy)prop 2 en 1 one; 1 (4 nitrophenyl) 3 phenyl 3 (quinolin 6 yloxy)prop 2 en 1 one; 1 ethyl 1 methyl 4 oxo 4 phenyl 2 (quinolin 6 yloxy)but 2 en 1 yl benzoate; 1 phenyl 3 (5 phenyl 1h pyrrol 2 yl) 3 (quinolin 6 yloxy)prop 2 en 1 one; 1 [3 oxo 1,3 diphenylprop 1 en 1 yl]quinolin 4(1h) one; 1,3 diphenyl 3 (quinolin 3 yloxy)prop 2 en 1 one; 1,3 diphenyl 3 (quinolin 6 yloxy)prop 2 en 1 ol; 1,3 diphenyl 3 (quinolin 6 yloxy)prop 2 en 1 one; 1,3 diphenyl 3 (quinolin 8 yloxy)prop 2 en 1 one; 3 ((3 benzoyl 2 phenylquinolin 6 yl)oxy) 1,3 diphenylprop 2 en 1 on; 3 (4 methylphenyl) 1 phenyl 3 (quinolin 6 yloxy)prop 2 en 1 one; 3 (5 (3 fluorophenyl) 1h pyrrol 2 yl) 1 phenyl 3 (quinolin 6 yloxy)prop 2 en 1 one; 3 phenyl 3 (quinolin 6 yloxy) 1 (2 thienyl)prop 2 en 1 one; 3 [(2 methylquinolin 4 yl)oxy] 1,3 diphenylprop 2 en 1 one; 3 [(4 methylquinolin 2 yl)oxy] 1,3 diphenylprop 2 en 1 one; acetylene derivative; acylacetylene; amodiaquine; chalcone; chloroquine; mefloquine; molecular scaffold; quinolinol derivative; quinolone derivative; unclassified drug; Article; chemical modification; drug structure; functionalization; nucleophilicity; one pot synthesis; priority journal; regioselectivity
Издатель
  • Elsevier Ltd
Тип документа
  • journal article
Тип лицензии Creative Commons
  • CC
Правовой статус документа
  • Свободная лицензия
Источник
  • scopus