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110 results on '"de Mattos, Marcio C. S."'

3. The Ritter reaction of N‐(hydroxymethyl)saccharin with nitriles.

Author

de Oliveira, Marllon Nascimento and de Mattos, Marcio C. S.

Subjects
*SACCHARIN, *HYDROXYMETHYL compounds, *NITRILES, *PHARMACEUTICAL chemistry, *AMIDES, *SCALABILITY
Abstract

The development of the Ritter reaction of N‐(hydroxymethyl)saccharin with nitriles for the synthesis of N‐[(saccharinyl)methyl]amides is reported. The success of this reaction relies on an operationally simple procedure and on the use of inexpensive reagents. The present method enables access to a variety of saccharin scaffolds of potential interest in medicinal chemistry in moderate to high yields. Furthermore, the scalability of this reaction was demonstrated by a multigram‐scale transformation, without any loss of efficiency. [ABSTRACT FROM AUTHOR]

Published
2024
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10. One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid.

Author

de Andrade, Vitor S. C. and de Mattos, Marcio C. S.

Subjects
*CHEMICAL reactions, *HETEROCYCLIC compounds, *THIOUREA, *PHENYLENEDIAMINES, *THIAZOLES, *QUINOXALINES
Abstract

A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for a-monohalogenation of ß-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced the corresponding 2-aminothiazoles in up to 87% yield. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process. [ABSTRACT FROM AUTHOR]

Published
2018
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13. Efficient Direct Halogenation of Unsymmetrical N-Benzyl- and N-Phenylureas with Trihaloisocyanuric Acids.

Author

Sanabria, Carlos M., Costa, Bruno B. S., Viana, Gil M., de Aguiar, Lúcia C. S., and de Mattos, Marcio C. S.

Subjects
HALOGENATION, PHENYLUREA compounds, BENZYL compounds, TRIFLUOROACETIC acid, ACETONITRILE
Abstract

A simple and efficient methodology for the direct halogenation of N-phenylureas was developed using trihaloisocyanuric acids in acetonitrile at room temperature. This protocol proved to be effective for the construction of N-phenylureas with different patterns of substitution. Additionally, less reactive N-benzylureas were halogenated in the presence of a mixture of trifluoroacetic acid and acetonitrile at room temperature. [ABSTRACT FROM AUTHOR]

Published
2018
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16. Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid.

Author

Sanabria, Carlos M., do Casal, Mariana T., de Souza, Raphael B. A., de Aguiar, Lúcia C. S., and de Mattos, Marcio C. S.

Subjects
IODINATION, REGIOSELECTIVITY (Chemistry), PHENYLUREA compounds, ACETONITRILE, SUBSTITUTION reactions
Abstract

An efficient regioselective iodination of N-phenylureas was developed using iodine/trichloroisocyanuric acid in acetonitrile at room temperature. This protocol proved to be effective on a broad range of substituted N-phenylureas, forming the p-iodinated compounds in 65-96% yield under mild and neutral conditions. [ABSTRACT FROM AUTHOR]

Published
2017
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40. Tribromoisocyanuric Acid in Trifluoroacetic Acid: An Efficient System for Smooth Brominating of Moderately Deactivated Arenes.

Author

de Almeida, Leonardo S., de Mattos, Marcio C. S., and Esteves, Pierre M.

Subjects
*TRIFLUOROACETIC acid, *BROMINATION, *AROMATIC compounds, *ORGANIC cyclic compounds, *ORGANIC synthesis
Abstract

Moderately deactivated arenes are efficiently brominated by the reaction with tribromoisocyanuric acid (0.34 mol equiv) in trifluoroacetic acid at room temperature in 48-85% isolated yield. This medium avoids the polybromination of the substrate, observed in the same reaction performed in 98% H2SO4. [ABSTRACT FROM AUTHOR]

Published
2013
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42. Superelectrophilic Iodination of Deactivated Arenes with Triiodoisocyanuric Acid.

Author

Esteves, Pierre M. and de Mattos, Marcio C. S.

Subjects
*AROMATIC compounds, *CHEMICAL reagents, *DISSOCIATION (Chemistry), *ELECTROPHILES, *HALOGENATION
Abstract

The reaction of triiodoisocyanuric acid (TICA) with deactivated arenes in acidic medium led to the efficient and regioselective formation of the corresponding iodoarenes, in 55-88% isolated yield. The acidity of the medium was found to be the most important factor influencing the electrophilic iodination of weakly nucleophilic substrates by TICA. [ABSTRACT FROM AUTHOR]

Published
2011
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43. Addition of Thio Compounds to ( R )-Limonene Catalyzed by Amberlyst-15.

Author

De Mattos, Marcio C. S. and Sanseverino, Antonio M.

Subjects
*ION exchange resins, *LIMONITE, *ALKENES, *FLOTATION, *CATALYSTS
Abstract

The addition of thioacids and thiophenol to ( R )-limonene catalyzed by Amberlyst-15 produced the corresponding 9-thioester- or 9-thioether-p-menthene chemo- and regioselectively. [ABSTRACT FROM AUTHOR]

Published
2004
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44. Surface-Mediated Hydrohalogenation of Isoprene: A Facile Preparation of Prenyl Halides.

Author

de Mattos, Marcio C. S. and Manzolillo Sanseverino, Antonio

Subjects
*ISOPRENE, *HALIDES, *CHEMICAL reactions, *SILICA, *SILICA gel
Abstract

The reaction of isoprene with SOCl2 (0.5 mol equiv.) or PBr3 (0.4 mol equiv.) or PI3 (0.4 mol equiv.) in the presence of SiO2 at -10°C produced prenyl chloride (82%), or bromide (70%) or iodide (65%), respectively, in less than 30 min reaction time. [ABSTRACT FROM AUTHOR]

Published
2003
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46. A Green Preparation of N-Chloro- and N-Bromosaccharin.

Author

de Souza, Soraia P. L., da Silva, Joaquim F. M., and de Mattos, Marcio C. S.

Subjects
SODIUM salts, SACCHARIN, SUSTAINABLE chemistry, POTASSIUM chloride
Abstract

The reaction of the sodium salt of saccharin, potassium chloride or bromide and oxone® in water at room temperature for 24 h produced pure N-chloro- and N-bromosaccharin in 58% and 64% yield, respectively. [ABSTRACT FROM AUTHOR]

Published
2003
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