Mild, Simple, and Efficient Method for
            <i>N</i>
            -Formylation of Secondary Amines via Reimer–Tiemann Reaction

Shastri, Lokesh A.; Shastri, Samundeeswari L.; Bathula, Chinna; Basanagouda, Mahantesha; Kulkarni, Manohar V.

doi:10.1080/00397910903576644

Cited by 21 publications

(7 citation statements)

References 20 publications

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“…UV-visible and EPR spectra confirmed the presence of S 3 ˙ − in solutions of K 2 S in N -methylpyrrolidone (NMP). 46 Jiang et al proposed a reasonable mechanism for this multicomponent reaction involving reaction of N -benzyl-1-(2-iodophenyl)methanamine 132d with dichlorocarbene 46–48 generated from CHCl 3 to produce intermediate 134 . Copper-catalysed sulfur insertion gives 135 , which affords carbene intermediate 136 under basic conditions.…”

Section: Reactions Involving S3˙− Generated In Situ From S2−mentioning

confidence: 99%

Applications of trisulfide radical anion S₃˙⁻ in organic synthesis

et al. 2023

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Section: Reactions Involving S3˙− Generated In Situ From S2−mentioning

confidence: 99%

Applications of trisulfide radical anion S₃˙⁻ in organic synthesis

et al. 2023

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“…A recent method used the Reimer-Tiemann (R-T) reaction to produce formamides from secondary amines (Scheme 7) [31]. Alkyl, cyclic, and N -methylaniline derivatives all produced formamides in good to excellent yields, but the best yields were obtained with cyclic amines.…”

Section: Stoichiometric Formylating Agentsmentioning

confidence: 99%

“…General mechanism of the formylation via the Reimer-Tiemann reaction. Scheme adapted from reference [31]. …”

Section: Stoichiometric Formylating Agentsmentioning

confidence: 99%

Formylation of Amines

2014

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“…Compound 29 was treated with acetyl chloride and pivaloyl chloride, respectively, to obtain the acylated derivatives 30 and 31 [27]. In the course of a Reimer-Tiemann reaction the formylpiperazinyl analogue 32 was prepared from 29 with sodium ethanolate and chloroform [28]. Reaction of 29 with potassium cyanate in a mildly acidic environment yielded the carboxamide 33.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure-Activity Relationships of New 2-Phenoxybenzamides with Antiplasmodial Activity

et al. 2021

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The 2-phenoxybenzamide 1 from the Medicines for Malaria Venture Malaria Box Project has shown promising multi-stage activity against different strains of P. falciparum. It was successfully synthesized via a retrosynthetic approach. Subsequently, twenty-one new derivatives were prepared and tested for their in vitro activity against blood stages of the NF54 strain of P. falciparum. Several insights into structure-activity relationships were revealed. The antiplasmodial activity and cytotoxicity of compounds strongly depended on the substitution pattern of the anilino partial structure as well as on the size of substituents. The diaryl ether partial structure had further impacts on the activity. Additionally, several physicochemical and pharmacokinetic parameters were calculated (log P, log D7.4 and ligand efficiency) or determined experimentally (passive permeability and CYP3A4 inhibition). The tert-butyl-4-{4-[2-(4-fluorophenoxy)-3-(trifluoromethyl)benzamido]phenyl}piperazine-1-carboxylate possesses high antiplasmodial activity against P. falciparum NF54 (PfNF54 IC50 = 0.2690 µM) and very low cytotoxicity (L-6 cells IC50 = 124.0 µM) resulting in an excellent selectivity index of 460. Compared to the lead structure 1 the antiplasmodial activity was improved as well as the physicochemical and some pharmacokinetic parameters.

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Mild, Simple, and Efficient Method for N -Formylation of Secondary Amines via Reimer–Tiemann Reaction

Cited by 21 publications

References 20 publications

Applications of trisulfide radical anion S₃˙⁻ in organic synthesis

Applications of trisulfide radical anion S₃˙⁻ in organic synthesis

Formylation of Amines

Synthesis and Structure-Activity Relationships of New 2-Phenoxybenzamides with Antiplasmodial Activity

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Mild, Simple, and Efficient Method for N -Formylation of Secondary Amines via Reimer–Tiemann Reaction

Cited by 21 publications

References 20 publications

Applications of trisulfide radical anion S3˙− in organic synthesis

Applications of trisulfide radical anion S3˙− in organic synthesis

Formylation of Amines

Synthesis and Structure-Activity Relationships of New 2-Phenoxybenzamides with Antiplasmodial Activity

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Product

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Applications of trisulfide radical anion S₃˙⁻ in organic synthesis

Applications of trisulfide radical anion S₃˙⁻ in organic synthesis