36147-03-2Relevant academic research and scientific papers
Nickel-Catalyzed Formal Aminocarbonylation of Secondary Benzyl Chlorides with Isocyanides
Wang, Yun,Huang, Wenyi,Wang, Chenglong,Qu, Jingping,Chen, Yifeng
supporting information, p. 4245 - 4249 (2020/06/27)
Phenylacetamides represent versatile feedstocks in synthetic chemistry, widely existing in drug molecules and natural products. Herein, we disclose a nickel-catalyzed formal aminocarbonylation of secondary benzyl chlorides with isocyanides yielding α-substituted phenylacetamide with steric hindrance, which is synthetically challenging via palladium-catalyzed aminocarbonylation. The reaction features wide functional group tolerance under mild conditions, highlighted by the tolerance of various aromatic halide (-Cl, -Br, -I) and heteroaromatic rings (pyridine and pyrazine).
Amine Activation: N-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
Zhu, Yan-Ping,Mampuys, Pieter,Sergeyev, Sergey,Ballet, Steven,Maes, Bert U. W.
, p. 2481 - 2498 (2017/07/22)
N-arylamino acid amides have been synthesized via a novel method based on N-arylamine activation into isothioureas followed by reaction with amino acids under iron catalysis. The activated N-arylamines are easily prepared using a three-component reaction with commercial reagents, tert-butylisocyanide and S-phenyl benzenethiosulfonate. The protocol shows a broad functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied. (Figure presented.).
Acylimidazolides as Versatile Synthetic Intermediates for the Preparation of Sterically Congested Amides and Ketones: A Practical Synthesis of Proscar
Bhattacharya, A.,Williams, J.M.,Amato, J.S.,Dolling, U.-H.,Grabowski, E.J.J.
, p. 2683 - 2690 (2007/10/02)
Acylimidazolides react with magnesium amides to produce carboxamides in excellent yields, whereas Fe(III) catalyzed cross coupling between acylimidazolide and Grignard reagents produce ketones in high yields.These methods were utilized to prepare the α-reductase inhibitor Proscar as well as various 17β-amide and ketone analogs of Δ1-4-aza-5α-androsten-3-one.
Experimental and Theoretical Study of the Reactivity of Primary and Secondary Enaminones toward Diphenylketene. A Comparison of AM1 and HAM/3 Semiempirical Methods
Eberlin, Marcos N.,Takahata, Yuji,Kascheres, Concetta
, p. 5150 - 5155 (2007/10/02)
Diazodiphenylethanone (1) reacts with acyclic enamino ketones 2 and enamino esters 3 to form products of electrophilic attack of diphenylketene at Cα (5) and nitrogen (6 and 7).The relative reactivity of the different enaminones was shown to be consistent with HOMO energies determined by the HAM/3 semiempirical method.However, this approach could not completely explain the reactivity of the cyclic enamino ketones 4, which, by HAM/3, show a high energy second HOMO corresponding to the nonbonded pair of electrons on oxygen.
