89656-44-0Relevant articles and documents
Electrophilic formamidines. Organometallic addition to 2-methoxy pyrrolidine or piperidine N-t-butyl formamidines. Formation of 2-substituted pyrrolidines and piperidines
Gottlieb,Meyers
, p. 4723 - 4726 (1990)
The title compounds were prepared by addition of Grignard reagents to methoxyformamidines 6 and 8 in ether at room temperature. Hydrolysis gives the free secondary amines, or in cases of volatile products, their thiourea derivatives.
Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions
Babij, Nicholas R.,Boothe, Jordan R.,McKenna, Grace M.,Fornwald, Ryan M.,Wolfe, John P.
, p. 4228 - 4243 (2019/05/04)
The synthesis of bicyclic ureas and sulfamides via palladium-catalyzed alkene carboamination reactions between aryl/alkenyl halides/triflates and alkenes bearing pendant cyclic sulfamides and ureas is described. The substrates for these reactions are gene
Regioselective synthesis of azetidines or pyrrolidines by selenium-induced cyclization of secondary homoallylic amines
Franck, Xavier,Leleu, Stéphane,Outurquin, Francis
scheme or table, p. 4437 - 4440 (2010/09/20)
Azetidines or pyrrolidines can be regioselectively obtained by selenocyclization of homoallylic amines, according to the double bond substitution.
Stereocontrol in N-directed hydroboration: Synthesis of amino alcohols related to the piperidine alkaloids
Wang, Guoqiang,Vedejs, Edwin
scheme or table, p. 1059 - 1061 (2009/08/15)
Treatment of 2-(2'-alkenyl)-piperidine boranes with iodine or triflic acid induces internal hydroboration with high regiocontrol, even with a terminal alkene (R H). Good stereocontrol is possible for the N-benzyl substrates. Comparisons with acyclic model
Studies toward labeling cytisine with [11C]phosgene: Rapid synthesis of a δ-lactam involving a new chemoselective lithiation-annulation method
Rouden, Jacques,Seitz, Thomas,Lemoucheux, Laurent,Lasne, Marie-Claire
, p. 3787 - 3793 (2007/10/03)
With the aim of the radiolabeling of cytisine, a potent agonist of nicotinic receptors, with [11C]-phosgene, the rapid synthesis of a lactam model of our target has been studied. The key step of the δ-lactam formation is a new chemoselective lithiation-annulation method, under high dilution, of a suitable piperidinylcarbamoyl chloride. This precursor was obtained from (2-hydroxyethyl)-piperidine in a linear synthetic sequence involving a Corey-Fuchs olefination of the corresponding aldehyde, followed by a selective reduction, using a diimide equivalent, of an iodoalkyne into a (Z)-iodopropene piperidine. This alkene served as main precursor to study the cyclization according to several procedures using phosgene as the required carbonylating reagent.
Synthesis of bridged azabicyclic compounds using radical translocation reactions of 1-(o-halogenobenzoyl)-2-(prop-2-enyl)-and -(prop-2-ynyl)-piperidines
Ikeda, Masazumi,Kugo, Yasuhiro,Sato, Tatsunori
, p. 1819 - 1824 (2007/10/03)
Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate 8a, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-azabicyclo[3.2.1]octane 14a (a 5-exo cyclisation product) in quantitative yield as a diastereomeric mixture (66:34). 1-(o-Bromobenzoyl)-2-(prop-2-enyl)piperidine 13 also gave the 8-azabicyclo-[3.2.1]octane 16 (75% as a diastereomeric mixture), along with the pyrido[2,1-a]isoindolone 17 (10%) and the simple reduction product 18 (5%). 1-(o-Iodobenzoyl)-2-[3-(trimethylsilyl)prop-2-ynyl]piperidine 23 afforded, in addition to the pyrido[2,1-a]isoindolone 25 (18%), the 8-azabicyclo-[3.2.1]octane 24 (75%) which was converted into the 6-oxo derivative 27. For comparison, the behaviour of the azetidine congener 31 was also examined.
On the Stereoselectivity of Nitrone Addition to α-Diphenylphosphinoylalkenes
Armstrong, Susan K.,Collington, Eric W.,Stonehouse, Jon,Warren, Stuart
, p. 2825 - 2832 (2007/10/02)
The title reaction was investigated for both achiral and α-chiral alkenes 1-3, and for cyclic and acyclic nitrones 4 and 8.In each case, addition to allyldiphenylphosphine oxide 1 gave a single isoxazolidine product.The configurations of these isoxazolidi
Syntheses of nitrogen heterocycles by means of amine-directed carbonylation and hydrocarbonylation
Zhang, Zhaoda,Ojima, Iwao
, p. 281 - 289 (2007/10/02)
Amine-directed carbonylation of 2-allylpiperidine (5) gives 8-methyl-1-azabicyclononan-9-one (7) with extremely high regio- and stereoselectivity, which is promoted by a stoichiometric amount of 2 in the presence of hydrogen chloride.A c
Addition of Allylboronates to Schiff Bases and to Oximes
Hoffmann, Reinhard W.,Eichler, Guenter,Endesfelder, Andreas
, p. 2000 - 2007 (2007/10/02)
Clean addition of allylboronates of Type 3 to Schiff bases 2 leads to the secondary homoallylamines 4.Analogous addition to the oximes 9 results in the formation of the hydroxylamines 13.The latter allow the generation of the primary homoallylamines 14.
