Highly efficient one-pot C-, N- and O-acylation of indolin-2-one analogs

Jha, Mukund; Blunt, Brian

doi:10.1016/j.tetlet.2009.08.057

Cited by 19 publications

(2 citation statements)

References 26 publications

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“…used DCC along with a small quantity of DMAP to facilitate reaction between indole‐3‐carboxaldehyde and 4‐pentynoic acid [17] . DMAP is considered a good acetylating agent for increasing the reaction rate [18] . Thus, various acid chlorides were tested for the acylation of indole‐3‐carboxaldehyde in the presence of the DMAP catalyst and triethylamine as the base, with the aim of reducing the reaction time and achieving a more stable synthesis of amides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N‐Acyl Indole‐3‐Carboxaldehyde Derivatives and Polyvinyl Alcohol Acetalization with 1‐Propionylindole‐3‐Carboxaldehyde

Perwin,

Mazumdar

2024

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A series of seven stable amide derivatives based on indole‐3‐carboxaldehyde were synthesized with high yields using various aliphatic and aromatic acyl chlorides, triethylamine and DMAP as the catalyst at room temperature. Structural characterization was performed using FT‐IR, 1 H‐NMR, 13C‐NMR and LC–MS techniques. To develop bioactive material, acetalization of water‐soluble polyvinyl alcohol was achieved by reacting one of the N‐acyl derivatives, 1‐propionylindole‐3‐carboxaldehyde, in the presence of a p‐TSA catalyst to form polyvinyl acetal with pendant bioactive groups. The polymer was analyzed using 1 H‐NMR, FT‐IR, TGA, DSC, FE‐SEM and EDX spectroscopic techniques. The polymer was water‐insoluble with enhanced thermal stability compared to pure polyvinyl alcohol. This approach for developing N‐acyl derivatives of indole‐3‐carboxaldehyde and then reacting one of the monomers with polyvinyl alcohol to improve its thermal properties and stability in humid conditions has proven successful.

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Section: Introductionmentioning

confidence: 99%

Synthesis of N‐Acyl Indole‐3‐Carboxaldehyde Derivatives and Polyvinyl Alcohol Acetalization with 1‐Propionylindole‐3‐Carboxaldehyde

Perwin,

Mazumdar

2024

ChemistrySelect

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“…This observation is further substantiated by one of our recent publications where a similar chemoselectivity is reported in the acetylation of indoline-2-thione (7) using acetic anhydride in the presence of a catalytic amount of 4-N,N-dimethylaminopyridine. 27 For comparison, we treated indolin-2-one with benzyl alcohol under similar conditions but the reaction did not proceed; this highlights the unique nucleophilicity of S in indoline-2-thiones with respect to the O at C-2 in indolin-2-one.…”

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confidence: 99%