Carbon tetrabromide mediated oxidative cyclocondensation of ketones and thioureas: an easy access to 2-aminothiazoles

Keshari, Twinkle; Kapoorr, Ritu; Yadav, Lal Dhar S.

doi:10.1016/j.tetlet.2015.08.064

Cited by 25 publications

(15 citation statements)

References 54 publications

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“…Purification of the crude product by flash column chromatography (SiO 2 EtOAc:PE 1:10) afforded 6aa (48 mg, 71%). 1 H and 13 C NMR data are identical to those reported in the literature …”

Section: Methodssupporting

confidence: 82%

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Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Javorskis

Orentas

2017

J. Org. Chem.

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Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products. The deprotection method developed is fully selective for N-arylsulfonamides, and the possibility to discriminate among various different sulfonamides is demonstrated.

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“…Purification of the crude product by flash column chromatography (SiO 2 EtOAc:PE 1:10) afforded 6aa (48 mg, 71%). 1 H and 13 C NMR data are identical to those reported in the literature …”

Section: Methodssupporting

confidence: 82%

“…1 H and 13 C NMR data are identical to those reported in the literature. 61 3-Nitroaniline (6ab). Following general procedure IV using 5ab (104 mg, 0.26 mmol, 1.0 equiv) and TfOH (0.05 mL, 0.57 mmol, 2.2 equiv) at 80 °C.…”

Section: N-butyl-4-methyl-n-(3-((4-nitrophenyl)sulfonamido)phenyl)ben...mentioning

confidence: 99%

Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Javorskis

Orentas

2017

J. Org. Chem.

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“…Some of these methods include the following: NaICl 2 , [20] O 2 /KI/[Bmim]OTf, [21] and CBr 4 / Et 3 N, [22] and Fe 3 O 4 @SiO 2 .TiO 2 /NBS [23]. Despite the advantages of the previous methods, there is still a need to improve the synthesis of 2-aminothiazoles using new strategies and catalysts, due to the significant importance of the class of compounds in synthetic chemistry and pharmaceuticals.…”

Section: Introductionmentioning

confidence: 99%

Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles

Safari

Sadeghi

2016

Res Chem Intermed

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“…Recently, aminothiazoles derivatives were also synthesized by aqueous NaICl 2 , 13 carbon tetrabromaide, 14…”

Section: Quick Response Codementioning

confidence: 99%

Untitled

2018

IJPSR

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A quick one step, innovative approach for the Synthesis of 2aminothiazole derivatives from easily available thiourea and alkyl / aryl ketones with the help of Oxone and Iodobenzene reaction system has been developed in aqueous acetonitrile solution. The developed procedure is applicable to several types of substituted 2-aminothiazole derivatives to get the corresponding products. The developed methodology offers mild reaction condition, short reaction time, and moderate to admirable yields. This is one of the most simple and environmentally benign protocols for synthesis of 2aminothiazole derivatives. When reaction carried out in presence of oxone and Iodobenzene in aq. Acetonitrile solvent system there is formation of active Hypervalent iodine reagent in situ and that reagent is responsible for this conversion but, yield of reaction is less. We go in detailed in Hypervalent reagent study and got some literature in that researcher used catalytic KBr along with oxone and Iodobenzene and there is amplify in activity of Hypervalent iodine reagent because of catalytic amount of potassium bromide. So we decided to use catalytic amount of KBr along with oxone and Iodobenzene reagent and there is increase in yield of desirable product.

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Carbon tetrabromide mediated oxidative cyclocondensation of ketones and thioureas: an easy access to 2-aminothiazoles

Cited by 25 publications

References 54 publications

Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Montmorillonite K10: an effective catalyst for synthesis of 2-aminothiazoles

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