- Highly Efficient DMSO-Promoted α-Hydrolysis of α-Halohydroxamates under Mild Conditions
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A novel and efficient method for the nucleophilic α-hydrolysis of α-halohydroxamates with water under metal-free conditions is described. In this reaction, the simple and readily available dimethyl sulfoxide (DMSO) was used as a catalyst, while water serv
- Yoon Lee, Chang,Kim, Sung-Gon
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p. 1607 - 1614
(2021/02/26)
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- PRODUCTION METHOD FOR HYDROXY-CARBOXYLIC ACID AMIDE COMPOUND, AND NOVEL ARYLBORONIC ACID COMPOUND
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A method for production of hydroxycarboxylic acid amide compounds, comprising performing amide condensation between an α- or β-hydroxycarboxylic acid compound and an amine compound in the presence as a catalyst of an alkylboronic acid represented by R3B(OH)2 (wherein R3 is a primary alkyl group) or an arylboronic acid compound to produce a hydroxycarboxylic acid amide compound, the arylboronic acid compound being represented by Formula (1): (in Formula (1), -(CH2)nNR1R2 is bonded at an ortho position or a para position, n is 1 or 2, R1 is a tertiary alkyl group, R2 is a secondary or tertiary alkyl group, and -NR1R2 may be a ring).
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Paragraph 0045; 0047
(2015/01/18)
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- MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines
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For efficient direct amide condensations, a new class of catalysts are developed by immobilizing boronic acids on mesocellular siliceous foam. Associated with their large pores, the microenvironments surrounding the immobilized active species greatly influence the catalytic activity. The fluoroalkyl moieties on the silica surface significantly enhance the catalytic performance along with easy recovery and reuse. This approach proposes a potential way to optimize various types of silica-supported catalysts. the Partner Organisations 2014.
- Gu, Liuqun,Lim, Jaehong,Cheong, Jian Liang,Lee, Su Seong
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supporting information
p. 7017 - 7019
(2014/06/23)
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- Primary alkylboronic acids as highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids
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Primary alkylboronic acids such as methylboronic acid and butylboronic acid are highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids. The catalytic activities of these primary alkylboronic acids are much higher than those of the previously reported arylboronic acids. The present method was easily applied to a large-scale synthesis, and 14 g of an amide was obtained in a single reaction.
- Yamashita, Risa,Sakakura, Akira,Ishihara, Kazuaki
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supporting information
p. 3654 - 3657
(2013/08/23)
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- On DABAL-Me3 promoted formation of amides
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The range and utility of DABAL-Me3 couplings of methyl esters and free carboxylic acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic acids derivatives. The influence of microwave energy on the reaction system was shown to be typically related to thermal effects (over-pressuring and superheating).
- Dubois, Nathalie,Glynn, Daniel,McInally, Thomas,Rhodes, Barrie,Woodward, Simon,Irvine, Derek J.,Dodds, Chris
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supporting information
p. 9890 - 9897
(2013/10/22)
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- Bromoamides as starting materials in the synthesis of α-hydroxy- and α- alkoxy derivatives
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Silver oxide promotes substitution of the bromine at position 2 of α- bromocarboxamides, with a hydroxyl or an alkoxyl group.
- Cavicchioni
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p. 2223 - 2227
(2007/10/02)
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- ETHER-AMIDES AND GLYCOSIDE-AMIDES FROM 2-BROMOISOBUTYRAMIDES AND SACCHARIDES BEARING A FREE PRIMARY, SECONDARY OR ANOMERIC ALCOHOLIC GROUP
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Glycoylamides were obtained in high yields in the presence of silver oxide at room temperature from 2-bromoisobutyramides and the partially protected monosaccharides, 1,2:3,4-di-O-isopropylidene-D-galactopyranose, 5, 1,2:5,6-di-O-isopropylidene-D-glucofuranose, 6, and 2,3,4,6-tetra-O-benzyl-D-glucopyranose, 7.Full characterization through 1H and 13C NMR spectra has been achieved.
- Catelani, Giorgio,Nejad, Farzaneh Moftakhari Kamrani,D'Angeli, Ferruccio,Cavicchioni, Giorgio,Marchetti, Paolo
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- CHEMISTRY OF 2-BROMO-2-METHYLPROPANAMIDES. SYNTHESIS AND SOLVOLYTIC BEHAVIOUR OF OXAZOLIDINONES AND SPIRO-OXAZOLIDINONES
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The base-promoted reaction of 2-bromo-2-methylpropanamides (1) with 5-, 6-, and 7-membered lactams (2) affords spiro-oxazolidinones (3).The latter compounds are hydrolysed under acidic conditions to yield the ω-aminoester amides (7).The solvolytic behaviour of some monocyclic oxazolidinones obtained upon reaction of common amides with 2-bromoamides (1) is also reported.
- Scrimin, Paolo,Cavicchioni, Giorgio,D'Angeli, Ferruccio,Goldblum, Amiram,Maran, Flavio
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