Synthesis of 2 carbon‐14 analogue of thioflavanones

Basooti, Mohammad; Saadatjoo, Naghi; Nemati, Firozeh; Shirvani, Gholamhossein; Faghih, Mohammad Amin Ahmadi; Javaheri, Mohsen

doi:10.1002/jlcr.3533

Cited by 3 publications

(1 citation statement)

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“…The direct condensation seems to occur by intramolecular nucleophilic attack of the sulfur anion of 70 to the arylaldehydes and subsequent elimination of lithium hydroxide (Scheme 35). 52 This method was further utilized for the synthesis of carbonyl‐ 14 C‐labeled thioflavanone in 85% yield 53 . 2′‐Mercaptoacetophenone was also condensed with n ‐heptaldehyde in the presence of 0.5 equiv of pyrrolidine in toluene for 3 h at reflux, to give 2‐( n ‐heptyl)thiochroman‐4‐one (Scheme 35).…”

Section: Synthesis Of Thioflavanonesmentioning

confidence: 99%

Synthetic Approaches to 2‐Alkylthiochroman‐4‐ones and Thioflavanones

Lee

2021

Bulletin Korean Chem Soc

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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 CF3SO3H, 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.

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Section: Synthesis Of Thioflavanonesmentioning

confidence: 99%