27829-43-2Relevant academic research and scientific papers
New Efficient Eco-Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti-Inflammatory Properties
Charlet, Rogatien,Da?ch, Adam,Dufrénoy, Pierrick,Ghinet, Alina,Hechelski, Marie,Jawhara, Samir,Waterlot, Christophe
, (2020/02/20)
A new environmentally friendly approach for the synthesis of idrocilamide (1), a marketed myorelaxant and anti-inflammatory agent, is reported herein. The synthetic strategy involves a solvent-free aminolysis reaction catalyzed by zinc-containing species
Microwave-assisted aminocarbonylation of ynamides by using catalytic [Fe3(CO)12] at low pressures of carbon monoxide
Pizzetti, Marianna,Russo, Adele,Petricci, Elena
supporting information; experimental part, p. 4523 - 4528 (2011/06/20)
The microwave-assisted aminocarbonylation of ynamides at low pressures of CO is reported. A new class of (E)-acrylamides that are potentially suitable for several applications has been regioselectively synthesized after microwave irradiation for only 20 min by using eco-friendly [Fe3(CO) 12] as the catalyst precursor and triethylamine as the ligand. This transformation is atom economic as all reactants are used in stoichiometric quantities. Furthermore, the transformation is efficiently applied to the alkoxycarbonylation of alkynes as well. Moreover, running these reactions under microwave irradiation allows the simplification of the reaction conditions with remarkable reductions in time, temperature and gas pressure.
Oxidative amidation and azidation of aldehydes by NHC catalysis
De Sarkar, Suman,Studer, Armido
supporting information; experimental part, p. 1992 - 1995 (2010/07/10)
Figure presented N-Heterocyclic carbene catalyzed oxidative amidations of various aldehydes to the corresponding hexafluoroisopropylesters by using the readily available organic oxidant A are described. The hexafluoroisopropylesters prepared in situ are shown to be highly useful active esters for amide bond formation. In addition, oxidative azidation of aldehydes is presented. These mild organocatalytic processes do not use any transition metal.
Michael Addition of Malononitrile to α-Acetylcinnamamides
Martin, Nazario,Martinez-Grau, Angeles,Seoane, Carlos,Marco, Jose L.,Albert, Armando,Cano, Felix H.
, p. 801 - 804 (2007/10/02)
The reaction of α-acetylcinnamamides 7a-e with malononitrile using piperidine as the catalyst is described.When one or two equivalents of malononitrile are used, the 2-amino-4H-pyran 6a or the polyfunctionalized carbocycles 9b-e, respectively, can be isolated as major products, depending on the experimental conditions.Compounds 9b-e apparently arise from a sequential Michael plus Knoevenagel addition of two molecules of malononitrile followed by Thorpe cyclization.The structure of 9b was determined by an X-ray crystallographic analysis, which revealed a twisted cyclohexadiene ring with characteristic crystal packing.Key Words: Cinnamamides, α-acetyl / Malononitrile / 4H-Pyrans / Michael additions
Study of the Transamidative Ring Expansion of N-ω-Halogenoalkyl-β-lactams of Alkyl Chain Lengths 2-12 in Liquid Ammonia and Other Liquid Amines: Syntheses of 7-, 8- and 9-Membered 1,5-Diaza Cyclic Ketones, including Routes to (+/-)-Dihydroperiphylline and (+/-)-Celabenzine
Begley, Michael J.,Crombie, Leslie,Haigh, David,Jones, Raymond C. F.,Osborne, Steven,Webster, Richard A. B.
, p. 2027 - 2046 (2007/10/02)
N-(3-Halogenopropyl)-4-phenylazetidin-2-ones undergo amination in liquid ammonia followed by transamidative ring expansion to give the eight-membered 4-phenyl-1,5-diazacyclooctan-2-one in excellent yield.Ring expansion of the amines in liquid ammonia is found to be much more effective than in hydrocarbon solvents.Formation of 7-, 8-, and 9-membered azalactams from the requisite ω-halogenoalkyl-β-lactams is an excellent synthetic process, though it is not applicable to 10-membered rings.In the case of rings of 13-, 15- and 17-members, although amination and apparent expansion takes place, the large rings appear not to be stable to ammonia and the final products are acyclic amides.N--4-phenylazetidin-2-one satisfactorily forms a 9-membered (Z)-olefinic azalactam, but the (E)-isomer gives an acyclic amino amide.By using alkyl-substituted β-lactam side-chains, C-substituted medium rings can be obtained; the relative instability of N-acyl β-lactams to ammonia, however, leads to acylamino amides rather than expanded rings.Employing ethylamine in place of ammonia, it is shown that N-ethylated azalactams are formed satisfactorily, and using allylamine, N-allyl medium rings capable of further elaboration are obtained.The chemistry of these systems is discussed.Using transamidation in liquid ammonia, a short synthesis of the 9-membered spermidine alkaloid (+/-)-dihydroperiphylline is reported.Synthesis of key intermediates, whose transformation into the 13-membered alkaloids of the celabenzine group has already been effected, has been carried out.X-Ray single-crystal structure determinations for 4-phenyl-1,5-diazacyclononan-2-one, trans-4-phenyl-8-methyl-1,5-diazacyclooctan-2-one and (Z)-4-phenyl-1,5-diazacyclonon-7-en-2-one are reported, and comment is made on certain conformational features.
