55814-36-3Relevant academic research and scientific papers
Nickel/Briphos-Catalyzed Direct Transamidation of Unactivated Secondary Amides Using Trimethylsilyl Chloride
Yu, Subeen,Shin, Taeil,Zhang, Maosheng,Xia, Yuanzhi,Kim, Hyunwoo,Lee, Sunwoo
supporting information, p. 7563 - 7566 (2019/01/03)
Direct transamidation of secondary amides was developed via nickel catalysis. In the presence of trimethylsilyl chloride and manganese, Ni(diglyme)Cl2 with a Briphos ligand efficiently promoted the transamidation of N-aryl benzamide derivatives with primary amines to afford the corresponding secondary amides in moderate to good yields. Primary amines bearing electron-donating groups gave higher yields of the transamidation products.
Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes
Cheung, Chi Wai,Ma, Jun-An,Hu, Xile
supporting information, p. 6789 - 6792 (2018/05/29)
Amides are an important class of organic compounds, which have widespread industrial applications. Transamidation of amides is a convenient method to generate new amides from existing ones. Tertiary amides, however, are challenging substrates for transamidation. Here we describe an unconventional approach to the transamidation of tertiary amides using nitroarenes as the nitrogen source under reductive conditions. Manganese metal alone mediates the reactions and no additional catalyst is required. The method exhibits broad scope and high functional group tolerance.
Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters
Dardir, Amira H.,Melvin, Patrick R.,Davis, Ryan. M.,Hazari, Nilay,Mohadjer Beromi, Megan
supporting information, p. 469 - 477 (2018/02/19)
Esters are valuable electrophiles for cross-coupling due to their ubiquity and ease of synthesis. However, harsh conditions are traditionally required for the effective cross-coupling of ester substrates. Utilizing a recently discovered precatalyst, Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig reactions involving cleavage of the C(acyl)-O bond of aryl esters that proceed under mild conditions are reported. The Pd(II) precatalyst is highly active because it is reduced to the Pd(0) active species more rapidly than previous precatalysts.
Cross-Coupling of Primary Amides to Aryl and Heteroaryl Partners Using (DiMeIHeptCl)Pd Promoted by Trialkylboranes or B(C6F5)3
Sharif, Sepideh,Day, Jonathan,Hunter, Howard N.,Lu, Yu,Mitchell, David,Rodriguez, Michael J.,Organ, Michael G.
supporting information, p. 18436 - 18439 (2018/01/08)
Boron-derived Lewis acids have been shown to effectively promote the coupling of amide nucleophiles to a wide variety of oxidative addition partners using Pd-NHC catalysts. Through a combination of NMR spectroscopy and control studies with and without oxygen and radical scavengers, we propose that boron-imidates form under the basic reaction conditions that aid coordination of nitrogen to Pd(II), which is rate limiting, and directly delivers the intermediate for reductive elimination.
Copper-Catalyzed sp3 C-H Aminative Cyclization of 2-Alkyl-N-arylbenzamides: An Approach for the Synthesis of N-Aryl-isoindolinones
Nozawa-Kumada, Kanako,Kadokawa, Jun,Kameyama, Takehiro,Kondo, Yoshinori
supporting information, p. 4479 - 4481 (2015/09/28)
The synthesis of isoindolinones via copper-catalyzed sp3 C-H functionalization of 2-alkyl-N-substituted benzamides is described. This process does not require the preparation of halogenated substitutes, expensive transition metals, or toxic Sn or CO gas. This method provides an efficient approach to generate various functionalized isoindolinones.
SPIRO-QUINAZOLINONE DERIVATIVES USEFUL FOR THE TREATMENT OF NEUROLOGICAL DISEASES AND CONDITIONS
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Page/Page column 112, (2014/08/19)
The present invention relates to novel spiro-quinazolinone derivatives as positive allosteric modulators for modulating metabotropic glutamate receptor subtype 4 (mGluR4) and/or altering glutamate level or glutamatergic signalling
N-Oxides and Related Compounds. Part 60. Novel Thermal and Photochemical Rearrangements of N-Substituted 2-Pyridones
Katritzky, Alan R.,Chapman, Andrew V.,Cook, Michael J.,Millet, George H.
, p. 2743 - 2754 (2007/10/02)
Examples of four novel rearrangements of derivatives of 1-hydroxy-4,6-diphenyl-2-pyridone are reported: all involve N-O fission and formation of 3-substituted or both 3- and 5-substituted-4,6-diphenyl-2-pyridones. (a) 1-OCH2CH2R (R = vinyl or phenyl) compounds give 3-CH2R (R = vinyl or phenyl) derivatives with elimination of CH2O. (b) The 1-octyloxy-compound gives the 3-octyloxy-derivative by simple transposition. (c) 1-Acyloxy-compounds form the corresponding 3- and 5-acyloxy-2-pyridones. (d) 1-Imidoyloxy-compounds yield the rearranged 3- and 5-amido-2-pyridones.The mechanisms probably all involve homolytic N-O fission.
Process for producing 2-alkylbenzanilide
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, (2008/06/13)
2-Alkylbenzanilide is produced by reacting an alkyl 2-alkylbenzoate having the formula STR1 wherein X represents a lower alkyl group and R represents a lower alkyl group with an aniline having the formula STR2 wherein Y represents hydrogen atom, an alkoxy
