54520-83-1Relevant academic research and scientific papers
Superacid promoted reactions of N-acyliminium salts and evidence for the involvement of superelectrophiles
Zhang, Yiliang,DeSchepper, Daniel J.,Gilbert, Thomas M.,Sai, Kiran Kumar S.,Klumpp, Douglas A.
, p. 4032 - 4034 (2007)
Experimental and theoretical studies suggest the involvement of dicationic, superelectrophilic N-acyliminium ions in conversions catalyzed by superacids. The Royal Society of Chemistry.
Palladium-catalyzed C - O hydrogenolysis in γ-hydroxy γ-lactams as an efficient approach to 5-alkyl(aryl)pyrrolidin-2-ones
Turova,Berezhnaya,Starodubtseva,Ferapontov,Vinogradov
, p. 859 - 863 (2015/12/24)
5-R-Pyrrolidin-2-ones were synthesized by Pd/Sibunit-catalyzed C - O hydrogenolysis of 5-R-5-hydroxypyrrolidin-2-ones with molecular hydrogen.
Enamine trapping with the oxidation of nicotine and analogues
Moehrle,Berlitz
experimental part, p. 219 - 226 (2010/08/05)
Various N-tertiary pyrrolidine derivatives 1 and 6-9 bearing voluminous substituents in 2-position react with Hg(II)-EDTA under double dehydrogenation and an atypical direction to the secondary C-5 with formation of the corresponding lactams 2 and 12-15. The primary products of a two electron withdrawal cannot be isolated. By addition of substituted benzaldehydes b-d as trapping reagents to the Hg(II)-EDTA solution additionally are received condensation products of the type of benzylidene lactams 1b-d, 6b,c and 7b-9b. Here the total yield of isolated products increases, while simultaneously the yield of unsubstituted lactams of the type 2 and 12-15 decreases. Therefore the atypical direction of dehydrogenation with the trapping aldehydes is the same as with the lactam forming pyrrolidines. Additionally the detection of the enamine species in the first stage of dehydrogenation with following reaction to the condensation product is secured. The (E)-configuration of 1b is confirmed by the chemical shift of the proton a-H and the 19F/13C-coupling constant of C-4 by direct comparison with its (Z)-isomer 27. The similar signal dates of the enone protons in the other prepared benzylidene lactams 1c,d, as well as 6b,c and 7b-9b verify also the (E)-configuration.
Oxidation 2-substituierter pyrrolidine und piperidine als nicotinanaloga
M?hrle, Hans,Berlitz, Johannes
experimental part, p. 985 - 992 (2009/03/11)
The oxidation of nicotine (1) with Hg(II)-EDTA follows the direction to the α-methylene group of the pyrrolidine part and results in a two-step dehydrogenation to lactam 3. The same course is observed with the aromatic or heteroaromatic 2-substituted comp
Synthesis of pyrrolidin-2-ones by 5-endo-trigonal radical cyclisation of N-vinyl-2,2-bis(phenylsulfanyl)acetamides
sato, Tatsunori,Chono, Noriko,Ishibashi, Hiroyuki,Ikeda, Masazumi
, p. 1115 - 1120 (2007/10/02)
A series of N-methyl-N-(1-substituted or 1,2-disubstituted vinyl)-2,2-bis(phenylsulfanyl)acetamides, upon treatment with tributyltin hydride in the presence of a catalytic amount of AIBN in boiling toluene, underwent smooth cyclisation in a 5-endo-trig ma
A NEW APPROACH TO 5-ARYLPYRROLIDIN-2-ONES VIA 5-ENDO-TRIG RADICAL CYCLIZATION OF α-HALO- OR α-THIO-SUBSTITUTED N-(1-ARYLETHENYL)ACETAMIDES
Sato, Tatsunori,Machigashira, Naomi,Ishibashi, Hiroyuki,Ikeda, Masazumi
, p. 139 - 142 (2007/10/02)
N-(1-Phenylethenyl)carbamoylmethyl radicals generated by tributyltin hydride-mediated cleavage of carbon-halogen or carbon-sulfur bond underwent smooth cyclization in a "disfavored" 5-endo-trig manner to give 5-phenylpyrrolidin-2-one.This method was applied to the synthesis of (+/-)-cotinine.
Decarboxylation of pyroglutamic acids with P2O5/CH3SO:3H: A general synthesis of 5-aryl-2-pyrrolidinones
Rigo,Fasseur,Cherepy,Couturier
, p. 7057 - 7060 (2007/10/02)
Treatment of pyroglutamic acids with acyl-activating reagents (P2O5/CH3SO3H, PPE....), possibly in the presence of triethylamine, yields acyl iminium salts, that can react in-situ with aromatic compounds to give
Friedel-Crafts Reactions. IV. The Use of Cyclic N-Formyl-2-Methoxyamines in Electrophilic Amidoalkylation of Aromatic Compounds
Malmberg, Mats,Nyberg, Klas
, p. 411 - 418 (2007/10/02)
Aromatic compounds react with cyclic N-formyl-2-methoxyamines in proton or Lewis acid catalyzed reactions, yielding 2-aryl substituted nitrogen heterocyclic compounds.These products are easily converted to the corresponding N-H and N-CH3 derivatives by acid hydrolysis and LiAlH4 reduction, respectively.
