Dess–Martin periodinane mediated synthesis of thioesters from aldehydes

Bandgar, Sunita B.; Bandgar, B. P.; Korbad, Balaji L.; Sawant, Sanjay S.

doi:10.1016/j.tetlet.2006.12.024

Cited by 52 publications

(23 citation statements)

References 45 publications

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“… 32 , 33 Bandgar et al reported Dess–Martin periodinane (DMP)-mediated reaction of aldehyde and thiol to produce corresponding thioester derivatives. 34 TfOH-catalyzed direct thioesterification of carboxylic acids using thiol was done by Iimura et al 35 Synthesis of thioesters via ruthenium-catalyzed olefin cross-metathesis with thioacrylate was reported by van Zijl et al 13 These two methods were also effective in the synthesis of α,β-unsaturated thioesters. 13 , 35 However, the synthesis of α,β-unsaturated thioesters by the direct thioesterification of the α,β-unsaturated acid, e.g., p -hydroxycinnamic acid, which itself has functional groups susceptible toward the self-esterification, is troublesome and protection of such functional group(s) (e.g., −OH group) is required to get better yield.…”

Section: Resultsmentioning

confidence: 99%

Fluorescent Small Molecules Are BIG Enough To Sense Biomacromolecule: Synthesis of Aromatic Thioesters and Understanding Their Interactions with ctDNA

Mallick¹,

Karmakar²,

Batuta³

et al. 2018

ACS Omega

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The visible fluorescent chromophoric moiety present in the water-soluble photoactive yellow protein (PYP) of Ectothiorhodospira halophila is p-hydroxycinnamic acid linked to the cysteine residue (Cys-69) by a thioester bond and it controls the key photoinduced biological processes of the host organism. In the present work, we have synthesized and characterized three structurally different thiophenyl esters [viz., p-hydroxycinnamic-thiophenyl ester (1), p-N,N-dimethylaminocinnamic-thiophenyl ester (2), and S-phenyl-3-(4-chlorophenyl)-3-(phenylthio)propanethioate (3)] in addition to a novel (to the best of our knowledge) stilbene-type olefinic compound, N1,N1,N2,N2-tetramethyl-1,2-bis(phenylthio)ethene-1,2-diamine (4), under the same reaction condition. All of these four compounds showed characteristic and distinguishable chromophoric/fluorophoric behavior in ethanol and also at pH 7.4. However, we have observed that the intrinsic chromophoric/fluorophoric activities of (1) and (2) were greatly influenced during their interactions with calf-thymus DNA, studied by a range of spectroscopic and physicochemical measurements. We have also applied density functional theory [B3LYP, 6-311G+(d,p)]-based method to get optimized structures of (1) and (2), which were explored further for molecular docking studies to understand their mode of interaction with DNA. The present study opens up their possible applications as fluorescence probes for biomacromolecules like DNA in future.

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Section: Resultsmentioning

confidence: 99%

Fluorescent Small Molecules Are BIG Enough To Sense Biomacromolecule: Synthesis of Aromatic Thioesters and Understanding Their Interactions with ctDNA

Mallick¹,

Karmakar²,

Batuta³

et al. 2018

ACS Omega

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“…However, the direct oxidative thioesterification of aldehydes or alcohols is still largely elusive. To the best of our knowledge,4 the available thioesterifications with aldehydes usually require the use of azide intermediates,5 azo‐type radical initiators6 and carbene catalysts7 (Scheme ). These methods often suffer from limitations, such as low scope of the substrates, complex systems, expensive or hazardous reagents.…”

Section: Methodsmentioning

confidence: 99%

Tetraethylammonium Bromide‐Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols

et al. 2013

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“…of Dess-Martin periodinane and 6.5 equiv. of NaN 3 in DCM at room temperature (Scheme 4) [41]. Various aromatic, heteroaromatic, and aliphatic aldehydes were used to establish the general applicability of this metal-free cross-coupling reaction.…”

Section: Metal-free Reactionsmentioning

confidence: 99%

Methods for the direct synthesis of thioesters from aldehydes: a focus review

Jabarullah

Jermsittiparsert

Melnikov

et al. 2019

Journal of Sulfur Chemistry

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Direct C-H bond functionalization chemistry allows the pot-, atom-, and step-economical and original construction of carbon-carbon and carbon-heteroatom bonds starting from hydrocarbons (or hydrocarbon fragments) without requiring pre-functionalization of the starting materials. In this context, synthesis of biologically and synthetically important thioesters through direct thioesterification of aldehydes has recently attracted considerable attention from organic synthetic communities, because aldehydes are cheap and widely abundant chemical materials. This review highlights up-todate developments and accomplishments in this interesting research arena with special emphasis on the mechanistic aspects of the reactions.

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Dess–Martin periodinane mediated synthesis of thioesters from aldehydes

Cited by 52 publications

References 45 publications

Fluorescent Small Molecules Are BIG Enough To Sense Biomacromolecule: Synthesis of Aromatic Thioesters and Understanding Their Interactions with ctDNA

Fluorescent Small Molecules Are BIG Enough To Sense Biomacromolecule: Synthesis of Aromatic Thioesters and Understanding Their Interactions with ctDNA

Tetraethylammonium Bromide‐Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols

Methods for the direct synthesis of thioesters from aldehydes: a focus review

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