- Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst
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Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.
- Singha, Krishnadipti,Ghosh, Subhash Chandra,Panda, Asit Baran
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supporting information
p. 657 - 662
(2021/02/02)
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- Direct Amidation of Carboxylic Acids through an Active α-Acyl Enol Ester Intermediate
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The development of a highly efficient and simple protocol for the direct amidation of carboxylic acids is described employing ynoates as novel coupling reagents. The transformation proceeds in good to excellent yields via in situ α-acyl enol ester intermediates formation under mild reaction conditions. This useful method has been demonstrated for a range of substrates to provide a succinct access to structurally diverse amides, including key intermediates of glibenclamide, tiapride hydrochloride, and nateglinide, and can be conducted on a mole scale.
- Xu, Xianjun,Feng, Huangdi,Huang, Liliang,Liu, Xiaohui
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p. 7962 - 7969
(2018/06/18)
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- The Broad Aryl Acid Specificity of the Amide Bond Synthetase McbA Suggests Potential for the Biocatalytic Synthesis of Amides
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Amide bond formation is one of the most important reactions in pharmaceutical synthetic chemistry. The development of sustainable methods for amide bond formation, including those that are catalyzed by enzymes, is therefore of significant interest. The ATP-dependent amide bond synthetase (ABS) enzyme McbA, from Marinactinospora thermotolerans, catalyzes the formation of amides as part of the biosynthetic pathway towards the marinacarboline secondary metabolites. The reaction proceeds via an adenylate intermediate, with both adenylation and amidation steps catalyzed within one active site. In this study, McbA was applied to the synthesis of pharmaceutical-type amides from a range of aryl carboxylic acids with partner amines provided at 1–5 molar equivalents. The structure of McbA revealed the structural determinants of aryl acid substrate tolerance and differences in conformation associated with the two half reactions catalyzed. The catalytic performance of McbA, coupled with the structure, suggest that this and other ABS enzymes may be engineered for applications in the sustainable synthesis of pharmaceutically relevant (chiral) amides.
- Petchey, Mark,Cuetos, Anibal,Rowlinson, Benjamin,Dannevald, Stephanie,Frese, Amina,Sutton, Peter W.,Lovelock, Sarah,Lloyd, Richard C.,Fairlamb, Ian J. S.,Grogan, Gideon
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supporting information
p. 11584 - 11588
(2018/09/10)
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- Oxidative activation of dihydropyridine amides to reactive acyl donors
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Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields. This journal is
- Funder, Erik Daa,Trads, Julie B.,Gothelf, Kurt V.
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p. 185 - 198
(2015/01/16)
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- Ni-catalyzed direct reductive amidation via C-O bond cleavage
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A novel Ni-catalyzed reductive amidation of C(sp2)-O and C(sp3)-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.
- Correa, Arkaitz,Martin, Ruben
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supporting information
p. 7253 - 7256
(2014/06/09)
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- Zinc(II)-catalyzed oxidative amidation of arylaldehydes with alkylamines under solvent-free conditions
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The first zinc-catalyzed oxidative amidation of arylaldehydes has been developed. Various amides were prepared in good yields under solvent-free and mild reaction conditions.
- Zhang, Min,Wu, Xiao-Feng
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supporting information
p. 1059 - 1062
(2013/04/10)
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- Diacetoxyiodobenzene mediated one-pot synthesis of diverse carboxamides from aldehydes
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A novel, one-pot, and highly facile protocol has been devised for an easy access of a series of novel glycosyl carboxamides from aldehydes using diacetoxyiodobenzene in the presence of ionic liquid at ambient temperature.
- Prasad, Virendra,Kale, Raju R.,Mishra, Bhuwan B.,Kumar, Dhananjay,Tiwari, Vinod K.
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supporting information; experimental part
p. 2936 - 2939
(2012/08/07)
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- Phencyclidine-like Effects of Tetrahydroisoquinolines and Related Compounds
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A series of 1,2,3,4-tetrahydroisoquinolines, tetrahydrothienopyridines, and related compounds were evaluated for their ability to inhibit binding of -1--N-allylnormetazocine to phencyclidine (PCP) and ? receptors, respectively.A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia.All of the compounds caused stereotyped behavior and ataxia, indicating their agonist actions at the PCP site.
- Gray, Nancy M.,Cheng, Brian K.,Mick, Stephen J.,Lair, Cecelia M.,Contreras, Patricia C.
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p. 1242 - 1248
(2007/10/02)
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