10283-95-1Relevant articles and documents
Electrochemical anion pool synthesis of amides with concurrent benzyl ester synthesis
Mevan Dissanayake,Melville, Alex D.,Vannucci, Aaron K.
, p. 3165 - 3171 (2019)
An electrosynthesis method for amide bond formation has been developed in an attempt to increase the atom economy for this class of reactions. This "anion pool" method electrochemically generates strong nucleophiles from amine substrates. The amine nucleophiles then react with acid anhydrides to generate amides, and the by-product from this reaction undergoes further chemical transformations to generate pharmaceutically relevant benzoic esters. These one-pot reactions are operationally simple, are performed at room temperature, and avoid rare transition metals and added bases. The amide synthesis is amenable to primary and secondary amines and a variety of anhydrides with yields up to 90% obtained. Atom economy and process mass index (PMI) values calculated for this procedure indicate that this process can be considered greener compared to traditional amide synthesis routes used by industry. Furthermore, this electrochemical approach showed unique selectivity when substrates that contained two inequivalent amine moieties were examined.
Direct oxidative amidation of benzyl alcohols using EDTA@Cu(II) functionalized superparamagnetic nanoparticles
Azizi, Kobra,Karimi, Meghdad,Nikbakht, Fatemeh,Heydari, Akbar
, p. 336 - 343 (2014)
Superparamagnetic Fe3O4@EDTA-Cu(II) nanoparticles were readily prepared and identified as an effective catalyst for the tandem transformation of benzyl alcohols and amine hydrochloride salts into the corresponding amides with tert-bu
Nickel/briphos-catalyzed transamidation of unactivated tertiary amides
Kim, Hyunwoo,Lee, Sunwoo,Shin, Taeil,Yang, Dahyeon
, p. 6053 - 6057 (2020)
The transamidation of tertiary amides was achieved via nickel catalysis in combination with briphos ligands. N-Methyl-N-phenylbenzamide derivatives reacted with primary amines in the presence of NiCl2/briphos L4 to provide the transamidated products in moderate to good yields. Primary aromatic amines delivered higher product yields than aliphatic amines.
Photochemistry of Epoxynaphthoquinones. 8. Endo-Stereoselective Photocycloaddition of 2,3-Epoxy-2,3-dihydro-2,3-dimethyl-1,4-naphthoquinone to Olefins Containing Amide Group
Maruyama, Kazuhiro,Osuka, Atsuhiro,Nakagawa, Katsuhiko
, p. 1021 - 1026 (1987)
Irradiation of a benzene solution of 2,3-epoxy-2,3-dihydro-2,3-dimethyl-1,4-naphthoquinone with olefins containing amide group, i.e., N-substituted acrylamides and N-allylcarboxamides predominantly gave the endo-cycloadducts.Upon further irradiation, the cycloadducts underwent photorearrangement to give spirophthalides and alkylidenephthalides.
Organophotoredox-Mediated Amide Synthesis by Coupling Alcohol and Amine through Aerobic Oxidation of Alcohol
Samanta, Samya,Shah, Sk. Sheriff,Shee, Maniklal,Singh, Amit Kumar,Singh, N. D. Pradeep,Venkatesh, Yarra
, (2020)
The combination of an organic photocatalyst [4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6 dicyanobenzene) or 5MeOCzBN (2,3,4,5,6-pentakis(3,6-dimethoxy-9 H-carbazol-9-yl)benzonitrile)], quinuclidine, and tetra-n-butylammonium phosphate (hydrogen-bonding catalyst) was employed for amide bond formations. The hydrogen-bonded OH group activated the adjacent C?H bond of alcohols towards hydrogen atom transfer (HAT) by a radical species. The quinuclidinium radical cation, generated through single-electron oxidation of quinuclidine by the photocatalyst, employed to abstract a hydrogen atom from the α-C?H bond of alcohols selectively due to a polarity effect-produced α-hydroxyalkyl radical, which subsequently converted to the corresponding aldehyde under aerobic conditions. Then the coupling of the aldehyde and an amine formed a hemiaminal intermediate that upon photocatalytic oxidation produced the amide.
Esters and amides from activated alcohols using manganese(IV) dioxide: Tandem oxidation processes
Foot, Jonathan S.,Kanno, Hisashi,Giblin, Gerard M. P.,Taylor, Richard J. K.
, p. 1055 - 1064 (2003)
Manganese(IV) dioxide can be used in conjunction with sodium cyanide in THF-methanol or in methanol alone for the direct conversion of activated alcohols into methyl esters. Ethyl and isopropyl esters can also be prepared. Similarly, use of manganese(IV) dioxide and sodium cyanide in THF containing ammonia or primary amines can be used to convert alcohols into the corresponding amides. Several activated alcohols and one non-activated alcohol example are reported.
Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines
Gilbert, Audrey,Bertrand, Xavier,Paquin, Jean-Fran?ois
, p. 7257 - 7260 (2018)
The synthesis of 5-[(pentafluorosulfanyl)methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)propyl]amide to occur without elimination of the chlorine atom, a reaction
Synthesis of cyclopropylpyrrolidines via reaction of N-allyl-N-propargylamides with a molybdenum carbene complex. Effect of substituents and reaction conditions
Harvey, Daniel F.,Sigano, Dina M.
, p. 2268 - 2272 (1996)
Previous studies have demonstrated that group 6 carbene complexes react with α,ω-enynes to form vinylcyclopropane derivatives in good to excellent yield, and that the length and composition of the tether between the alkyne and the alkene often has a dramatic impact on the viability of this reaction pathway. The reactivity of allylpropargyl amine derivatives with pentacarbonyl(1-methoxypentylidene)molybdenum(0) (14a) was investigated in order to provide further insight into the steric and electronic factors controlling this reaction. Treatment of allylpropargyl amines with 14a failed to produce the desired cyclization products while treatment of allylpropargyl amides with 14a led to the expected cyclopropylpyrrolidine systems in good to excellent yields. Higher yields are obtained when the reaction is conducted in a sealed vial in the presence of atmospheric oxygen.
Visible-light-induced radical cyclization of N-allylbenzamides with CF3SO2Na to trifluoromethylated dihydroisoquinolinones in water at room temperature
Zou, Long,Li, Pinhua,Wang, Bin,Wang, Lei
, p. 3362 - 3369 (2019)
A green and efficient strategy for the preparation of trifluoromethylated dihydroisoquinolinones via visible-light-induced radical cyclization of N-allylbenzamides with CF3SO2Na in water at room temperature was developed. This photoinduced reaction generated the desired products in good to excellent yields under simple and mild conditions.
Transition-metal-free oxidative amidation of benzyl alcohols with amines catalyzed by NaI: A new method for the synthesis of benzamides Dedicated to the memory of Professor Ahmad Sodagar
Karimi, Meghdad,Saberi, Dariush,Azizi, Kobra,Arefi, Marzban,Heydari, Akbar
, p. 5351 - 5353 (2014)
A simple, inexpensive, and efficient method for the synthesis of benzamides via the reaction of benzyl alcohols and amine hydrochloride salts in the presence of NaI as a green catalyst is described. Various derivatives of benzamide were synthesized in moderate to good yields using this method.
Visible Light-Driven, One-pot Amide Synthesis Catalyzed by the B12 Model Complex under Aerobic Conditions
Tian, Hui,Shimakoshi, Hisashi,Ono, Toshikazu,Hisaeda, Yoshio
, p. 237 - 240 (2019)
A visible light responsive catalytic system with the B12 complex as the catalyst and [Ir(dtbbpy)(ppy)2]PF6 as the photosensitizer was developed. It provides a convenient and efficient way to synthesize amides. Based on this method, trichlorinated organic compounds were converted into amides in the presence of an amine under aerobic conditions at room temperature in a one-pot procedure. Various trichlorinated organic compounds and an amine source, such as primary, secondary, and cyclic amines, have been evaluated for this transformation, providing the expected products in moderate to excellent yields. Notably, product formation depended on the reaction atmosphere where the amide was obtained under aerobic conditions while partially dechlorinated products were obtained under anaerobic conditions. As this protocol is free from hazardous reagents, extra additives, noble metals, and dangerous gas, the present method provides a novel and efficient approach for amide synthesis under mild and easily controlled conditions.
Site-Selective Installation of N?-Modified Sidechains into Peptide and Protein Scaffolds via Visible-Light-Mediated Desulfurative C–C Bond Formation
Griffiths, Rhys C.,Layfield, Robert,Long, Jed E.,Mitchell, Nicholas J.,Oldham, Neil J.,Scott, Daniel,Smith, Frances R.,Williams, Huw E. L.
supporting information, (2021/12/08)
Post-translational modifications (PTMs) enhance the repertoire of protein function and mediate or influence the activity of many cellular processes. The preparation of site-specifically and homogeneously modified proteins, to apply as tools to understand the biological role of PTMs, is a challenging task. Herein, we describe a visible-light-mediated desulfurative C(sp3)–C(sp3) bond forming reaction that enables the site-selective installation of N?-modified sidechains into peptides and proteins of interest. Rapid, operationally simple, and tolerant to ambient atmosphere, we demonstrate the installation of a range of lysine (Lys) PTMs into model peptide systems and showcase the potential of this technology by site-selectively installing an N?Ac sidechain into recombinantly expressed ubiquitin (Ub).
Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides
Zhang, Xinyu,Lin, Bo,Chen, Jianhui,Chen, Jiajia,Luo, Yanshu,Xia, Yuanzhi
, p. 819 - 825 (2021/02/01)
The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.
