The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Rajeev, Narasimhamurthy; Swaroop, Toreshettahally R.; Alrawashdeh, Ahmad I.; Rahman, Shofiur; Alodhayb, Abdullah; Anil, Seegehalli M; Kiran, Kuppalli R.; Chandra,; Georghiou, Paris E.; Rangappa, Kanchugarakoppal S.; Sadashiva, M. P.

doi:10.3762/bjoc.16.18

Cited by 10 publications

(2 citation statements)

References 36 publications

(33 reference statements)

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“…In continuation of our efforts in organic synthesis [38][39][40][41][42][43][44] we have recently reported the synthesis of quinoxalines, 45,46 thiazoles 47 and benzoxazoles 45 from a-ketodithioesters. In this direction, we have recently reported the synthesis of a-ketothioamides and explored their applications for the synthesis of 3,5-bis(acyl)-1,2,4-thiadiazoles.…”

Section: Introductionmentioning

confidence: 99%

A panoramic view on synthetic applications of α-oxothioamides: a highly regioselective synthesis of 2-acyl-4-(het)arylthiazoles and thioethers

et al. 2023

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Section: Introductionmentioning

confidence: 99%

A panoramic view on synthetic applications of α-oxothioamides: a highly regioselective synthesis of 2-acyl-4-(het)arylthiazoles and thioethers

et al. 2023

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“…The required organosulfur intermediates were prepared following our previously reported protocol. 18j b c e g h j The progress of the reactions was continuously monitored using TLC on pre-coated sheets of silica gel (Merck 60F254, 0.25 mm thickness). Visualization of the TLC plates was achieved using UV light.…”

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confidence: 99%

An Efficient Copper-Mediated Route for the Synthesis of 2-Substituted Benzothiazoles from Dithioesters and Investigation of Their Antibacterial Activities

Sadashiva,

Sukrutha,

Kiran

et al. 2023

Synthesis

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An efficient one-pot synthesis of 2-aryl/aroyl benzothiazoles has been developed through copper-mediated condensation of 2-chloroaniline with dithioesters. The method provides good isolated yields and exhibits broad functional group tolerance, accommodating both electron-donating and electron-withdrawing groups on the substrate. A series of synthesized compounds was evaluated for their antibacterial activity against Klebsiella pneumoniae, Pseudomonas aeruginosa, and Salmonella paratyphi. Among the series, compounds 4n, 5q, and 5r exhibited a significant inhibitory effect against the tested pathogens. Compound 5r demonstrated potential as an effective compound in both the agar well diffusion assay and broth microdilution assay. Additionally, compounds 4n, 5q, and 5r displayed strong inhibitory effects on biofilm formation of the pathogens in both the Crystal violet assay and MTT assay at a concentration of 10 mM. These findings highlight the promising antimicrobial and anti-biofilm properties of these compounds, indicating their potential for further investigation as potential therapeutic agents against the tested pathogens.

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Claisen type Condensation of Methyl Ketones with Carbimidothioates: A New Gateway for the Synthesis of β‐Enaminones

2021

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Carbimidothioates are synthesized by the reaction of Grignard reagents or heteroaryl lithium compounds with arylisothiocyanates followed by treatment with methyl iodide. Further, application of these intermediates in the synthesis of β‐enaminones by their condensation with methyl ketones in the presence of sodium hydride in DMF is reported. This method offers a new gateway for the synthesis of β‐enaminones, which are important building blocks in synthetic organic chemistry.

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The reaction of arylmethyl isocyanides and arylmethylamines with xanthate esters: a facile and unexpected synthesis of carbamothioates

Cited by 10 publications

References 36 publications

A panoramic view on synthetic applications of α-oxothioamides: a highly regioselective synthesis of 2-acyl-4-(het)arylthiazoles and thioethers

A panoramic view on synthetic applications of α-oxothioamides: a highly regioselective synthesis of 2-acyl-4-(het)arylthiazoles and thioethers

An Efficient Copper-Mediated Route for the Synthesis of 2-Substituted Benzothiazoles from Dithioesters and Investigation of Their Antibacterial Activities

Claisen type Condensation of Methyl Ketones with Carbimidothioates: A New Gateway for the Synthesis of β‐Enaminones

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