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Journal articles on the topic 'Amide bond formation'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 April 2022

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1

Kamanna, Kantharaju, S. Y. Khatavi, and P. B. Hiremath. "Microwave-assisted One-pot Synthesis of Amide Bond using WEB." Current Microwave Chemistry 7, no. 1 (2020): 50–59. http://dx.doi.org/10.2174/2213335606666190828114344.

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Background: Amide bond plays a key role in medicinal chemistry, and the analysis of bioactive molecular database revealed that the carboxamide group appears in more than 25% of the existing database drugs. Typically amide bonds are formed from the union of carboxylic acid and amine; however, the product formation does not occur spontaneously. Several synthetic methods have been reported for amide bond formation in literature. Present work demonstrated simple and eco-friendly amide bond formation using carboxylic acid and primary amines through in situ generation of O-acylurea. The reaction was

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2

Joullie, Madeleine M., and Kenneth M. Lassen. "Evolution of amide bond formation." Arkivoc 2010, no. 8 (2010): 189–250. http://dx.doi.org/10.3998/ark.5550190.0011.816.

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3

Hollanders, Karlijn, Bert Maes, and Steven Ballet. "A New Wave of Amide Bond Formations for Peptide Synthesis." Synthesis 51, no. 11 (2019): 2261–77. http://dx.doi.org/10.1055/s-0037-1611773.

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The construction of peptidic amide bonds has become a daily laboratory practice by virtue of well-established ‘coupling reagents’. Nonetheless, inherent limitations connected to these classical coupling methods in terms of waste, safety and expense have yet to be conquered. Research efforts have been devoted to synthetic methods able to surpass these limitations. This short review focuses on the advances made in these ‘non-classical’ methods for amide bond formation with a specific application in peptide chemistry. It consists of two main sections: (i) novel carboxylic activation reagents, and

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4

Buchspies, Jonathan, Md Mahbubur Rahman, and Michal Szostak. "Transamidation of Amides and Amidation of Esters by Selective N–C(O)/O–C(O) Cleavage Mediated by Air- and Moisture-Stable Half-Sandwich Nickel(II)–NHC Complexes." Molecules 26, no. 1 (2021): 188. http://dx.doi.org/10.3390/molecules26010188.

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The formation of amide bonds represents one of the most fundamental processes in organic synthesis. Transition-metal-catalyzed activation of acyclic twisted amides has emerged as an increasingly powerful platform in synthesis. Herein, we report the transamidation of N-activated twisted amides by selective N–C(O) cleavage mediated by air- and moisture-stable half-sandwich Ni(II)–NHC (NHC = N-heterocyclic carbenes) complexes. We demonstrate that the readily available cyclopentadienyl complex, [CpNi(IPr)Cl] (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene), promotes highly selective transa

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5

Miyabe, Hideto. "Transition-Metal-Free Activation of Amide Bond by Arynes." Molecules 23, no. 9 (2018): 2145. http://dx.doi.org/10.3390/molecules23092145.

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Highly reactive arynes activate the N–C and C=O bonds of amide groups under transition metal-free conditions. This review highlights the insertion of arynes into the N–C and C=O bonds of the amide group. The insertion of arynes into the N–C bond gives the unstable four-membered ring intermediates, which are easily converted into ortho-disubstituted arenes. On the other hand, the selective insertion of arynes into the C=O bond is observed when the sterically less-hindered formamides are employed to give a reactive transient intermediate. Therefore, the trapping reactions of transient intermedia

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6

Hernández, José G., Karen J. Ardila-Fierro, Deborah Crawford, Stuart L. James, and Carsten Bolm. "Mechanoenzymatic peptide and amide bond formation." Green Chemistry 19, no. 11 (2017): 2620–25. http://dx.doi.org/10.1039/c7gc00615b.

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7

Montalbetti, Christian A. G. N., and Virginie Falque. "Amide bond formation and peptide coupling." Tetrahedron 61, no. 46 (2005): 10827–52. http://dx.doi.org/10.1016/j.tet.2005.08.031.

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8

de Figueiredo, Renata Marcia, Jean-Simon Suppo, and Jean-Marc Campagne. "Nonclassical Routes for Amide Bond Formation." Chemical Reviews 116, no. 19 (2016): 12029–122. http://dx.doi.org/10.1021/acs.chemrev.6b00237.

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9

Song, Wangze, Kun Dong, and Ming Li. "Visible Light-Induced Amide Bond Formation." Organic Letters 22, no. 2 (2019): 371–75. http://dx.doi.org/10.1021/acs.orglett.9b03905.

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10

Bode, Jeffrey W. "ChemInform Abstract: Reinventing Amide Bond Formation." ChemInform 44, no. 41 (2013): no. http://dx.doi.org/10.1002/chin.201341260.

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11

Martín, Nuria, and Francisco G. Cirujano. "Heterogeneous catalytic direct amide bond formation." Catalysis Communications 164 (April 2022): 106420. http://dx.doi.org/10.1016/j.catcom.2022.106420.

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12

Szostak, Michal, and Guangchen Li. "Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N–C/O–C Cleavage." Synthesis 52, no. 18 (2020): 2579–99. http://dx.doi.org/10.1055/s-0040-1707101.

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In the past several years, tremendous advances have been made in non-classical routes for amide bond formation that involve transamidation and amidation reactions of activated amides and esters. These new methods enable the formation of extremely valuable amide bonds via transition-metal-catalyzed, transition-metal-free, or metal-free pathways by exploiting chemoselective acyl C–X (X = N, O) cleavage under mild conditions. In a broadest sense, these reactions overcome the formidable challenge of activating C–N/C–O bonds of amides or esters by rationally tackling nN → π*C=O delocalization in am

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13

Tao, Jin. "Study of Modification Mechanism of Ultrafine Silica Modified by PAMAM." Applied Mechanics and Materials 217-219 (November 2012): 252–55. http://dx.doi.org/10.4028/www.scientific.net/amm.217-219.252.

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Ultrafine silicon dioxide were modified by -NH2-teminated poly(amido-amine) (PAMAM) dendrimers to improve their dispersibility in the coatings. The modification mechanism was studied through density functional theory (DFT) in the gas phase. Virous initial configurations of ion bound to PAMAM were established to investigate the structures and the energetics of the complexes. Two stable conformers are found: types A ( is bound to the amine site) and C ( is bound to the amide site). Types A and C indicate the chemical bond formation of Si-N and Si-O, respectively.

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14

Westerhausen, Matthias, Alexander N. Kneifel, Ivonne Lindner, Jelena Grčić, and Heinrich Nöth. "Dimeric Methylzinc Bis(2-pyridylmethyl)amide – Synthesis, Molecular Structure and Reaction with Dimethylzinc." Zeitschrift für Naturforschung B 59, no. 2 (2004): 161–66. http://dx.doi.org/10.1515/znb-2004-0207.

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The zincation of bis(2-pyridylmethyl)amine with dimethylzinc yields dimeric methylzinc bis(2-pyridylmethyl)amide (1) with a central Zn2N2 cycle with Zn-N distances of 204.8(5) and 209.8(4) pm. The Zn-C bond length of 197.0(5) pm lies in the characteristic region. The addition of dimethylzinc to 1 leads to an opening of the Zn2N2 cycle and the formation of tetramethyltrizinc bis[bis(2-pyridylmethyl)amide] (2). The dimethylzinc molecule coordinates to a pyridyl and an amide group, the C-Zn-C bond angle of 135.3(3) being rather large. In solution, compound 2 loses methane at room temperature and

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15

III, John W. Lippert. "Amide bond formation using amino acid fluorides." Arkivoc 2005, no. 14 (2005): 87–95. http://dx.doi.org/10.3998/ark.5550190.0006.e11.

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16

Davis, Anthony P., and John J. Walsh. "Amide bond formation via pentafluorothiophenyl active esters." Tetrahedron Letters 35, no. 27 (1994): 4865–68. http://dx.doi.org/10.1016/s0040-4039(00)76989-9.

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17

Allen, C. Liana, and Jonathan M. J. Williams. "Metal-catalysed approaches to amide bond formation." Chemical Society Reviews 40, no. 7 (2011): 3405. http://dx.doi.org/10.1039/c0cs00196a.

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18

Mizuno, Mamoru, Ikuyo Muramoto, Katsuaki Kobayashi, Hiroshi Yaginuma, and Toshiyuki Inazu. "The New Amide Bond Formation Using Trialkylphosphine." Phosphorus, Sulfur, and Silicon and the Related Elements 177, no. 8-9 (2002): 1945. http://dx.doi.org/10.1080/10426500213339.

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19

Narendar Reddy, Thatikonda, Adilson Beatriz, Vaidya Jayathirtha Rao, and Dênis Pires de Lima. "Carbonyl Compounds′ Journey to Amide Bond Formation." Chemistry - An Asian Journal 14, no. 3 (2019): 344–88. http://dx.doi.org/10.1002/asia.201801560.

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20

Yao, Haoyi, and Kana Yamamoto. "Aerobic Amide Bond Formation with N ‐hydroxysuccinimide." Chemistry – An Asian Journal 7, no. 7 (2012): 1542–45. http://dx.doi.org/10.1002/asia.201200017.

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21

Feng, J., M. F. Lv, G. P. Lu, and C. Cai. "Selective formation of C–N and CN bonds via C(sp3)–H activation of isochroman in the presence of DTBP." Organic Chemistry Frontiers 2, no. 1 (2015): 60–64. http://dx.doi.org/10.1039/c4qo00293h.

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An organocatalytic approach for the synthesis of isochroman derivatives via direct C(sp<sup>3</sup>)–H bond and N–H bond coupling is described. The C–N (amine or amide) and CN (imidate) products can be selectively achieved by controlling the amount of oxidants.

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22

Bisenieks, Egils, Janis Poikans, Aiva Plotniece, Eiva Bernotiene, Wei-Bor Tsai, and Arkadij Sobolev. "Sodium N-(3,5-Bis(ethoxycarbonyl)-2,6-dimethyl-1,4-dihydropyridine-4-carbonyl)-l-methioninate." Molbank 2020, no. 3 (2020): M1148. http://dx.doi.org/10.3390/m1148.

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The development of the methods for amide bond formation is important for various uses in the laboratory and industrial applications. The compounds combined in their structures 1,4-dihydroisonicotinic acids and amino acids linked with an amide bond can be considered as “privileged structures” due to their broad range of biological activities. Herein, the formation of amide bond between 1,4-dihydroisonicotinic acid and l-methionine is reported. The coupling of l-methionine with pentafluorophenyl active ester of 1,4-dihydroisonicotinic acid appears to be a convenient and effective method for amid

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23

Moreno-Fuquen, Rodolfo, Vanessa Melo, and Javier Ellena. "Crystal structure of 2-(4-chlorobenzamido)benzoic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 11 (2015): o856—o857. http://dx.doi.org/10.1107/s2056989015017879.

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In the title molecule, C14H10ClNO3, the amide C=O bond isantito theo-carboxy substituent in the adjacent benzene ring, a conformation that facilitates the formation of an intramolecular amide-N—H...O(carbonyl) hydrogen bond that closes anS(6) loop. The central amide segment is twisted away from the carboxy- and chloro-substituted benzene rings by 13.93 (17) and 15.26 (15)°, respectively. The most prominent supramolecular interactions in the crystal packing are carboxylic acid-H...O(carboxyl) hydrogen bonds that lead to centrosymmetric dimeric aggregates connected by eight-membered {...HOC=O}2s

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24

Wang, Xiaoling, Jing Li, and Yujiro Hayashi. "Oxidative peptide bond formation of glycine–amino acid using 2-(aminomethyl)malononitrile as a glycine unit." Chemical Communications 57, no. 35 (2021): 4283–86. http://dx.doi.org/10.1039/d1cc00130b.

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Amide linkage of glycine–amino acid was synthesized by coupling of substituted 2-(aminomethyl)malononitrile as a C-terminal glycine unit and N-terminal amine using CsOAc and O<sub>2</sub> in aqueous solution.

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25

Fulton, David A., Anthony R. Pease, and J. Fraser Stoddart. "Cyclodextrin-based carbohydrate clusters by amide bond formation." Israel Journal of Chemistry 40, no. 3-4 (2000): 325–33. http://dx.doi.org/10.1560/26tf-06hg-eqjj-w85j.

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26

Martí-Centelles, Vicente, M. Isabel Burguete, and Santiago V. Luis. "Macrocycle Synthesis by Chloride-Templated Amide Bond Formation." Journal of Organic Chemistry 81, no. 5 (2016): 2143–47. http://dx.doi.org/10.1021/acs.joc.5b02676.

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27

Wu, Xinghua, and Longqin Hu. "Amide bond formation from selenocarboxylates and aromatic azides." Tetrahedron Letters 46, no. 48 (2005): 8401–5. http://dx.doi.org/10.1016/j.tetlet.2005.09.145.

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28

Ulrich, Emily C., Despina J. Bougioukou, and Wilfred A. van der Donk. "Investigation of Amide Bond Formation during Dehydrophos Biosynthesis." ACS Chemical Biology 13, no. 3 (2018): 537–41. http://dx.doi.org/10.1021/acschembio.7b00949.

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29

Ben Halima, Taoufik, Jeanne Masson-Makdissi, and Stephen G. Newman. "Nickel-Catalyzed Amide Bond Formation from Methyl Esters." Angewandte Chemie 130, no. 39 (2018): 13107–11. http://dx.doi.org/10.1002/ange.201808560.

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30

Ben Halima, Taoufik, Jeanne Masson-Makdissi, and Stephen G. Newman. "Nickel-Catalyzed Amide Bond Formation from Methyl Esters." Angewandte Chemie International Edition 57, no. 39 (2018): 12925–29. http://dx.doi.org/10.1002/anie.201808560.

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31

Philpott, Helena K., Pamela J. Thomas, David Tew, Doug E. Fuerst, and Sarah L. Lovelock. "A versatile biosynthetic approach to amide bond formation." Green Chemistry 20, no. 15 (2018): 3426–31. http://dx.doi.org/10.1039/c8gc01697f.

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Combining N-acyltransferases and CoA ligases with desired substrate profiles allows the construction of non-natural biosynthetic pathways for the synthesis of structurally diverse secondary and tertiary amides in high yields.

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32

Zarecki, Adam P., Jacek L. Kolanowski, and Wojciech T. Markiewicz. "Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids." Molecules 25, no. 8 (2020): 1761. http://dx.doi.org/10.3390/molecules25081761.

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Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The

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33

Silva, Luana, Ricardo F. Affeldt, and Diogo S. Lüdtke. "Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation." Journal of Organic Chemistry 81, no. 13 (2016): 5464–73. http://dx.doi.org/10.1021/acs.joc.6b00832.

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34

Liu, Huizhen, Gabor Laurenczy, Ning Yan, and Paul J. Dyson. "Amide bond formation via C(sp3)–H bond functionalization and CO insertion." Chem. Commun. 50, no. 3 (2014): 341–43. http://dx.doi.org/10.1039/c3cc47015f.

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35

Punji, Benudhar, and Muniyappa Vijaykumar. "Advances in Transition-Metal-Catalyzed C–H Bond Oxygenation of Amides." Synthesis 53, no. 17 (2021): 2935–46. http://dx.doi.org/10.1055/a-1481-2584.

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AbstractC–O bond formation represents a fundamental chemical transformation in organic synthesis to develop valuably oxygenated (hetero)arenes. Particularly, the direct and regioselective C–H bond oxygenation of privileged amides, using a transition metal catalyst and a mild oxygenating source, is a step-economy and attractive approach. During the last decade, considerable progress has been realized in the direct C–H oxygenation of primary, secondary, and tertiary amides. This Short Review compiles the advances in transition-metal-catalyzed oxygenation of C(sp2)–H and C(sp3)–H bonds on various

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36

Naoum, Johnny N., Israel Alshanski, Agata Gitlin-Domagalska, Moshe Bentolila, Chaim Gilon, and Mattan Hurevich. "Diffusion-Enhanced Amide Bond Formation on a Solid Support." Organic Process Research & Development 23, no. 12 (2019): 2733–39. http://dx.doi.org/10.1021/acs.oprd.9b00398.

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37

Valeur, Eric, and Mark Bradley. "Amide bond formation: beyond the myth of coupling reagents." Chem. Soc. Rev. 38, no. 2 (2009): 606–31. http://dx.doi.org/10.1039/b701677h.

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38

Jumina, Dwi Siswanta, Mayliana Anggraeni, Muhamad Idham Darusalam Mardjan, Panut Mulyono, and Keisuke Ohto. "Calix[4]resorcinarene-Chitosan Hybrid via Amide Bond Formation." Asian Journal of Chemistry 27, no. 6 (2015): 2273–76. http://dx.doi.org/10.14233/ajchem.2015.18735.

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39

Sasaki, Kaname, and David Crich. "Facile Amide Bond Formation from Carboxylic Acids and Isocyanates." Organic Letters 13, no. 9 (2011): 2256–59. http://dx.doi.org/10.1021/ol200531k.

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40

Chalmet, S., W. Harb, and M. F. Ruiz-López. "Computer Simulation of Amide Bond Formation in Aqueous Solution." Journal of Physical Chemistry A 105, no. 51 (2001): 11574–81. http://dx.doi.org/10.1021/jp0135656.

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41

Allen, C. Liana, and Jonathan M. J. Williams. "ChemInform Abstract: Metal-Catalyzed Approaches to Amide Bond Formation." ChemInform 42, no. 48 (2011): no. http://dx.doi.org/10.1002/chin.201148241.

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42

Roose, B., M. J. O. Anteunis та D. Tavernier. "α-Cyano-β-styrenyl esters for amide bond formation". Bulletin des Sociétés Chimiques Belges 97, № 4 (2010): 267–70. http://dx.doi.org/10.1002/bscb.19880970405.

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43

Yao, Haoyi, and Kana Yamamoto. "ChemInform Abstract: Aerobic Amide Bond Formation with N-Hydroxysuccinimide." ChemInform 43, no. 45 (2012): no. http://dx.doi.org/10.1002/chin.201245060.

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44

DAVIS, A. P., and J. J. WALSH. "ChemInform Abstract: Amide Bond Formation via Pentafluorothiophenyl Active Esters." ChemInform 25, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199447082.

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45

Sayes, Morgane, and André B. Charette. "Diphenylsilane as a coupling reagent for amide bond formation." Green Chem. 19, no. 21 (2017): 5060–64. http://dx.doi.org/10.1039/c7gc02643a.

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46

Sabatini, Marco T., Lee T. Boulton, Helen F. Sneddon, and Tom D. Sheppard. "A green chemistry perspective on catalytic amide bond formation." Nature Catalysis 2, no. 1 (2019): 10–17. http://dx.doi.org/10.1038/s41929-018-0211-5.

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47

Blanco, María-Jesús, Jean-Claude Chambron, Valérie Heitz, and Jean-Pierre Sauvage. "A Linear Multiporphyrinic [2]-Rotaxane via Amide Bond Formation." Organic Letters 2, no. 20 (2000): 3051–54. http://dx.doi.org/10.1021/ol006137b.

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48

Hattori, Tomohiro, Wataru Muramatsu, and Hisashi Yamamoto. "Substrate-Controlled Amide Bond Formation: Innovation of Peptide Synthesis." Journal of Synthetic Organic Chemistry, Japan 79, no. 5 (2021): 382–90. http://dx.doi.org/10.5059/yukigoseikyokaishi.79.382.

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49

Pappin, Brighid B., Stephan M. Levonis, Peter C. Healy, Milton J. Kiefel, Michela I. Simone, and Todd A. Houston. "Crystallization-induced amide bond formation creates a boron-centered spirocyclic system." Heterocyclic Communications 23, no. 3 (2017): 167–69. http://dx.doi.org/10.1515/hc-2017-0023.

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AbstractThe 5-nitrosalicylate ester of 2-acetamidophenylboronic acid (C15H10BN2O6) is formed under crystallization conditions from the 5-nitrosalicylate ester of 2-aminophenylboronic acid. The boron at the center of this structure exists as a tetrahedral complex produced by a dative bond with the amide carbonyl. The perpendicular shape produces an unusual packing structure including a bifurcated hydrogen bond between the amide hydrogen and carbonyl groups on two neighboring molecules. We propose that this reaction occurs due to increased Lewis acidity of the nitrosalicylate ester of 2-aminophe

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50

Banerjee, Amit, and Hisashi Yamamoto. "Direct N–O bond formation via oxidation of amines with benzoyl peroxide." Chemical Science 10, no. 7 (2019): 2124–29. http://dx.doi.org/10.1039/c8sc04996c.

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A general, mild and efficient method for direct N–O bond formation starting from commercially available amines, benzoyl peroxide and Cs<sub>2</sub>CO<sub>3</sub> without undesirable C–N bond (amide) formation.

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