Synthetic Approaches to 2‐Alkylthiochroman‐4‐ones and Thioflavanones. (29th March 2021)

• Record Type: Journal Article
• Authors: In Lee, Jae
• Is Part Of: Bulletin of the Korean Chemical Society. Volume 42:Number 6(2021)
• Page Start: 852
• Page End: 862
• Publication Date: 2021-03-29
• Subjects: 2‐Alkylthiochroman‐4‐ones -- Thioflavanones -- Cyclodehydration -- 1, 4‐Addition -- Friedel–Crafts acylation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/bkcs.12272
• Languages: English
• ISSNs: 0253-2964

Abstract

Abstract : 2‐Alkylthiochroman‐4‐ones have been synthesized by acid‐catalyzed cyclodehydration of 3‐alkyl‐3‐(phenylthio)propanoic acids, Friedel–Crafts acylation of 3‐alkyl‐3‐(phenylthio)propanoyl chlorides with Lewis acids, direct reaction of thiophenols and acrylic acids using CF3 SO3 H, and 1, 4‐addition of organometallic reagents to thiochromones. Furthermore, thioflavanones have been synthesized by cyclization of 3‐phenyl‐3‐(phenylthio)propanoyl chlorides with Lewis acids, incorporation of sulfur atoms into 2'‐halochalcones and subsequent cycloelimination, 1, 4‐addition of S ‐protected chalcones, direct condensation of 2'‐mercaptoacetophenone with arylaldehydes using lithium diisopropylamide, conjugate addition of organometallic reagents to thiochromones, and hydrogenation of thioflavones. Abstract : Typical methods for the preparation of 2‐alkylthiochroman‐4‐ones and thioflavanones.