New route to the 5-((arylthio-and heteroarylthio) methylene)-3-(2, 2, 2-trifluoroethyl)-furan-2 (5H)-ones—Key intermediates in the synthesis of 4-aminoquinoline γ- …

…, A Lavoignat, S Picot, M Médebielle, JP Bouillon

Index: Kanishchev, Oleksandr S.; Lavoignat, Adeline; Picot, Stephane; Medebielle, Maurice; Bouillon, Jean-Philippe Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 22 p. 6167 - 6171

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Citation Number: 12

Abstract

Abstract In this Letter we report on a multi-step synthesis of 5-((arylthio-and heteroarylthio)- methylene)-3-(2, 2, 2-trifluoroethyl) furan-2 (5H)-ones starting from γ-keto thiolester or γ-keto carboxylic acid. The key intermediate γ-lactones were then reacted with 4-aminoquinoline- derived amines via ring opening—ring closure (RORC) process affording the corresponding γ-hydroxy-γ-lactams in moderate to good yields. In vitro antimalarial activity of the resulting ...