43219-52-9Relevant academic research and scientific papers
Palladium-Catalyzed Synthesis of Allylic Ureas via an Isocyanate Intermediate
Jay, Lucien P.,Barker, Timothy J.
, p. 1829 - 1831 (2016)
A palladium-catalyzed coupling of allylic carbonates with trimethylsilylisocyanate to provide allylic isocyanates is reported. Amines are added in a second step to yield allylic ureas in this one-pot procedure. Use of a bidentate phosphine ligand with a large bite angle was found to be important in this transformation. The scope of allylic carbonates has been examined, as well as amines compatible with these reaction conditions.
Rapid synthesis method of biomass-based amide
-
Paragraph 0046-0048; 0051, (2019/01/15)
The invention discloses a rapid synthesis method of biomass-based amide, which comprises the steps: formamide is used as an amine source, formic acid is used as a hydrogen source, biomass aldehyde andketone is used as a raw material, the direct addition of formamide and aldehyde and ketone components and the reduction of formic acid is promoted to prepare the corresponding formamide derivative byrapidly heating under microwave-assisted heating and in the absence of a solvent and a catalyst; the formamide derivative is selectively converted to the corresponding primary amide by alcoholysis under the action of a base. The microwave assisted heating reaction system of the invention has higher catalytic efficiency than the corresponding oil bath system, greatly shortens the reaction time, remarkably improves the selectivity. The conversion rate of the biomass aldehyde or ketone compound is at least 99%, and the yield of the formamide derivative can reach 85 to 99%; the formamide can be synthesized by alcoholysis to obtain a primary amide with a yield of 92 to 99%.
Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca
, p. 4814 - 4819 (2018/11/10)
A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).
Isonitrile alkylations: A rapid route to imidazo[1,5-a]pyridines
Li, Yajun,Chao, Allen,Fleming, Fraser F.
supporting information, p. 2111 - 2113 (2016/02/05)
Metalated arylmethylisonitriles readily add to 2-chloropyridines to afford imidazo[1,5-a]pyridines. Analogous additions to imidoyl chlorides and a chloroquinoline provide imidazoles and an imidazo[1,5-a]quinolone which, like imidazo[1,5-a]pyridines, are v
Efficient isocyanide-less isocyanide-based multicomponent reactions
Neochoritis, Constantinos G.,Stotani, Silvia,Mishra, Bhupendra,D?mling, Alexander
supporting information, p. 2002 - 2005 (2015/04/27)
Isocyanides are the Jekyll and Hyde of organic chemistry allowing for extremely interesting transformations that are not only extremely odorous but also noxious. Therefore, an isocyanide-less isocyanide-based multicomponent reaction (IMCR) has been developed, and this protocol is expected to replace many of the old procedures in the future not only in IMCR but in other areas of organic chemistry as well.
Substrate-directable heck reactions with arenediazonium salts. The regio- and stereoselective arylation of allylamine derivatives and applications in the synthesis of naftifine and abamines
Prediger, Patricia,Barbosa, Lais Ferreira,Genisson, Yves,Correia, Carlos Roque Duarte
experimental part, p. 7737 - 7749 (2011/12/01)
The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the car-bonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.
New Syntheses of Isomerically Pure Allyl and Propargyl Cyanides by Isocyanide-Cyanide Rearrangement
Wolber, Erwin K. A.,Schmittel, Michael,Ruechardt, Christoph
, p. 525 - 532 (2007/10/02)
A new route for the synthesis of isomerically pure allyl and propargyl cyanides has been developed.Allylic amines are synthesized from the corresponding alcohols by Mitsunobu or by Overman reaction.Formylation with formic acid derivatives provides N-substituted formamides, which are dehydrated to isocyanides. 1,2-Sigmatropic rearrangement by flash pyrolysis provides the isomerically pure allyl and propargyl cyanides. Key Words: Isocyanide-cyanide rearrangment / Cyanides, allyl- and propargyl-
