Direct synthesis of 2-/3-(trifluoromethyl)thiochroman-4-ones: Superacid-induced tandem alkylation-cyclic acylation of benzenethiols using 2-/3-(trifluoromethyl)acrylic acid

Prakash, G. K. Surya; Narayanan, Arjun; Nirmalchandar, Archith; Vaghoo, Habiba; Paknia, Farzaneh; Mathew, Thomas; Oláh, George A.

doi:10.1016/j.jfluchem.2016.08.013

Cited by 5 publications

(3 citation statements)

References 22 publications

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“…Construction of thiochromanone skeletons may follow one of a number of approaches, including Pd-catalyzed carbonylative heteroannulation of iodothiophenols with allenes and carbon monoxide, base-catalyzed cyclization of β-halopropanoic acids with arylthiophenols, base-catalyzed condensation of β-propiolactone with 2-ethylthiophenol followed by acid-promoted cyclization, and intramolecular Friedel−Crafts acylation with Lewis acids or methanesulfonic acid [ 16 ]. A recently described one-pot procedure employs a microwave-assisted protocol for the synthesis of 2-/3-methylthiochroman-4-ones by superacid-catalyzed alkylation followed by cyclic acylation [ 17 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Novel 2,2-Dimethylthiochromanones as Anti-Leishmanial Agents

et al. 2021

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Within this work, we describe the design and synthesis of a range of novel thiochromanones based on natural products reported to possess anti-leishmanial action, and their synthetic derivatives. All compounds were elaborated via the key intermediate 2,2,6-trimethoxythiochromanone, which was modified at the benzylic position to afford various ester, amine and amide analogues, substituted by chains of varying lipophilicity. Upon testing in Leishmania, IC50 values revealed the most potent compounds to be phenylalkenyl and haloalkyl amides 11a and 11e, with IC50 values of 10.5 and 7.2 μM, respectively.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Novel 2,2-Dimethylthiochromanones as Anti-Leishmanial Agents

et al. 2021

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“…However, side products such as diaryl sulfides and diaryl disulfides were formed in significant amounts. Similarly, 2‐(trifluoromethyl)thiochroman‐4‐ones were synthesized in 36–75% yields by the reaction of 3‐(trifluoromethyl)acrylic acid and thiophenols using CF 3 SO 3 H in CH 2 Cl 2 under microwave irradiation 23 …”

Section: Synthesis Of 2‐(alkyl)thiochroman‐4‐onesmentioning

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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“…Trifluoromethyl-substituted acrylic acids provides thiochrom-4-ones (from thiophenols) in good yields from triflic acid. 39 This chemistry was likewise useful in preparing trifluoromethyl-substituted indanones and dihydrocoumarins (Scheme 25). 40 Trifluoromethyl-substituted superelectrophiles, such as 96, are proposed in these transformations.…”

Section: Scheme 24mentioning

confidence: 99%

Superelectrophiles in ring-forming reactions

Klumpp¹,

Kennedy²,

Kotali³

2017

Arkivoc

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Superelectrophiles are inherently reactive species and there have been many recent applications of these intermediates in cyclization reactions. Diverse electrophilic centers have been utilized in these synthetic reactions including carboxonium, carbenium, carbonium, iminium, and other ions. This article describes these recent advances, dating from the last comprehensive review in 2007 up to June 2017.

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Direct synthesis of 2-/3-(trifluoromethyl)thiochroman-4-ones: Superacid-induced tandem alkylation-cyclic acylation of benzenethiols using 2-/3-(trifluoromethyl)acrylic acid

Cited by 5 publications

References 22 publications

Synthesis and Evaluation of Novel 2,2-Dimethylthiochromanones as Anti-Leishmanial Agents

Synthesis and Evaluation of Novel 2,2-Dimethylthiochromanones as Anti-Leishmanial Agents

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

Superelectrophiles in ring-forming reactions

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