77302-27-3Relevant academic research and scientific papers
Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies
Grams, R. Justin,Lawal, Monsurat M.,Szwetkowski, Connor,Foster, Daniel,Rosenblum, Carol Ann,Slebodnick, Carla,Welborn, Valerie Vaissier,Santos, Webster L.
supporting information, p. 172 - 178 (2021/10/14)
We report a chemoselective, phosphine-catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n-tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with (E)-stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α-carbon and the proton on the amide nitrogen is abstracted by the ?-carbon to furnish the (E)-acrylamides. DFT calculations revealed a clear energetic driving force for the (E)- over the (Z)-isomer. (Figure presented.).
Electrochemical oxidative cyclization of olefinic carbonyls with diselenides
Guan, Zhipeng,Wang, Yunkun,Wang, Huamin,Huang, Yange,Wang, Siyuan,Tang, Hongding,Zhang, Heng,Lei, Aiwen
supporting information, p. 4976 - 4980 (2019/09/30)
The tandem cyclization of olefinic carbonyls with easily accessible diselenides facilitated by electrochemical oxidation has been successfully developed, which provides an environmentally friendly method for the construction of C-Se and C-O bonds simultaneously. A series of seleno dihydrofurans and seleno oxazolines, bearing fragile heterocycles, subtle C-I bonds and supernumerary vinyl groups, were forged using this elegant chelation strategy. Neither metal catalysts nor external chemical oxidants are required to promote this transformation.
A cinnamide derivatives and use thereof
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Paragraph 0045-0048, (2019/07/04)
The invention discloses a cinnamide derivatives, its structure is shown as formula I: In the general formula (I): R selected from cyclopropyl, cyclobutyl, cyclopropyl methyl, allyl, trifluoroethyl or 2 - fluorophenyl. The invention also disclosed the abov
Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines
Gilbert, Audrey,Bertrand, Xavier,Paquin, Jean-Fran?ois
supporting information, p. 7257 - 7260 (2018/11/23)
The synthesis of 5-[(pentafluorosulfanyl)methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)propyl]amide to occur without elimination of the chlorine atom, a reaction
Iodine(III)-promoted synthesis of oxazolines from N-allylamides
Moon, Nicholas G.,Harned, Andrew M.
supporting information, p. 2960 - 2963 (2013/06/27)
PhI(OAc)2 (activated by BF3·OEt2) has been used to promote the oxidative cyclization of N-allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C-O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile.
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.
The triphenyl phosphite-chlorine reagent in the synthesis of pyrroles from N-allylamides
Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Prati, Fabio
, p. 995 - 998 (2007/10/03)
A novel application of (PhO)3P-Cl2 chemistry to the synthesis of 2-substituted and 2,3-disubstituted pyrroles from N-allyl-amides is illustrated. A mild procedure is used to generate the imino chloride intermediates, which are subseq
Synthesis of substituted 4-arylpiperidin-2-ones by a 6-exo-trig radical cyclization
Vila, Xavier,Zard, Samir Z.
, p. 45 - 50 (2007/10/03)
A series of 5-substituted-4-arylpiperidin-2-ones have been synthesized in a 4 step sequence involving a radical 6-exo-trig cyclization as the key step.
Organozirconium-mediated solution- and solid-phase synthesis of 3-benzyl pyrrolidines and other potentially neuroactive amines
Hunter, Rupert A.,Macfarlane, Donald P. S.,Whitby, Richard J.
, p. 3314 - 3318 (2008/09/18)
An efficient route to 3-benzylpyrrolidines using a zirconium-mediated cyclisation both in solution and on a solid support is reported. 3-Benzylidine-pyrrolidines, 3-aryl-pyrrolidines and 4-arylpiperidines were also synthesised. Georg Thieme Verlag Stuttga
