73153-44-3Relevant academic research and scientific papers
Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion
Li, Guangchen,Rahman, Md. Mahbubur,Szostak, Michal
, p. 1060 - 1066 (2020)
The direct nucleophilic addition to amides represents an attractive methodology in organic synthesis that tackles amidic resonance by ground-state destabilization. This approach has been recently accomplished with carbon, nitrogen and oxygen nucleophiles.
One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents
Ma, Jianting,Cui, Xue,Xu, Junyu,Tan, Yinfeng,Wang, Yan,Wang, Xuesong,Li, Youbin
supporting information, p. 3661 - 3667 (2022/02/07)
A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.
Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
Liu, Chengwei,Lalancette, Roger,Szostak, Roman,Szostak, Michal
supporting information, p. 7976 - 7981 (2019/10/10)
Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.
Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of N-Mesylamides by N-C Cleavage: Electronic Effect of the Mesyl Group
Liu, Chengwei,Liu, Yongmei,Liu, Ruzhang,Lalancette, Roger,Szostak, Roman,Szostak, Michal
, p. 1434 - 1437 (2017/03/23)
A general Pd-catalyzed Suzuki-Miyaura cross-coupling of N-mesylamides with arylboronic acids by selective N-C cleavage has been developed. The presented results represent the first example of a transition-metal-catalyzed cross-coupling of amides activated by an atom-economic, cheap, and benign mesyl group. The reaction delivers arylated products featuring a range of useful functional groups by chemoselective cleavage of the amide N-C bond with high efficiency. Both the scope and the origin of high selectivity are discussed. A beneficial effect of the N-mesyl substituent on the bond activation in acyclic amides is presented.
Decarbonylative Phosphorylation of Amides by Palladium and Nickel Catalysis: The Hirao Cross-Coupling of Amide Derivatives
Liu, Chengwei,Szostak, Michal
supporting information, p. 12718 - 12722 (2017/10/06)
Considering the ubiquity of organophosphorus compounds in organic synthesis, pharmaceutical discovery agrochemical crop protection and materials chemistry, new methods for their construction hold particular significance. A conventional method for the synthesis of C?P bonds involves cross-coupling of aryl halides and dialkyl phosphites (the Hirao reaction). We report a catalytic deamidative phosphorylation of a wide range of amides using a palladium or nickel catalyst giving aryl phosphonates in good to excellent yields. The present method tolerates a wide range of functional groups. The reaction constitutes the first example of a transition-metal-catalyzed generation of C?P bonds from amides. This redox-neutral protocol can be combined with site-selective conventional cross-coupling for the regioselective synthesis of potential pharmacophores. Mechanistic studies suggest an oxidative addition/transmetallation pathway. In light of the importance of amides and phosphonates as synthetic intermediates, we envision that this Pd and Ni-catalyzed C?P bond forming method will find broad application.
ZnO and ZnO-nanoparticles: Efficient and reusable heterogeneous catalysts for one-pot synthesis of N-acylsulfonamides and sulfonate esters
Tamaddon, Fatemeh,Sabeti, Mohammad Reza,Jafari, Abbas Ali,Tirgir, Farhang,Keshavarz, Elham
, p. 41 - 45 (2012/01/12)
Commercially available and preparative ZnO nanoparticles are reported as efficient and reusable catalysts for the chemoselective synthesis of N-acylsulfonamides and sulfonate esters. A one-pot sequential sulfonylation and acylation of amines took place to afford the N-acylsulfonamides in excellent yields under solvent-free conditions. The ZnO catalyst can be reused for without significant loss of catalytic activity.
Development of an acyl sulfonamide anti-proliferative agent, ly573636 ? na
Yates, Matthew H.,Kallman, Neil J.,Ley, Christopher P.,Wei, Jeffrey N.
experimental part, p. 255 - 262 (2010/04/22)
The synthesis of 5-bromo-thiophene-2-sulfonic acid 2,4-dichlo- robenzoylamide sodium salt on multikilogram scale is described. The initial clinical supplies were made using carbonyl diimidazole to converge the two fragments. A more efficient acid chloride process has been developed, which also provides better control of impurities and color throughout the synthesis.
α,α,α-Trichloromethylcarbonyl Compounds as Acylating Reagents of Amides
Atanassova, I.A.,Petrov, J.S.,Ognjanova, V.H.,Mollov, N.M.
, p. 2083 - 2090 (2007/10/02)
Various α,α,α-trichloromethylcarbonyl compounds, namely chloral, trichloroacetone, trichloracetophenone and benzyltrichloromethyl acetate are used in alkaline medium as acylating reagents for primary and secondary amides.
Radical Pair Mechanism in the Aromatic Rearrangement of O-Alkylsulfinyl-N-phenylhydroxylamines
Heesing, Albert,Kleine Homann, Walter,Muellers, Wolfgang
, p. 152 - 164 (2007/10/02)
O-Alkylsulfinyl-N-benzoyl-N-phenylhydroxylamines (3) rearrange at -70 degC to give sulfonamides 4, o-sulfones 5, p-sulfones 6, and o-sulfonates 7.These reactions proceed intramolecularly via the radical pair 13 by -, - and -shifts in both radicals as proved both by experiments with 18O-indicated N-benzoyl-N-phenylhydroxylamine (1) and by strong 13C-CIDNP effects.The third oxygen in the o-sulfonate 7 is donated by a second molecule of the educt 1.
