87813-03-4Relevant articles and documents
Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines
Buev, Evgeny M.,Moshkin, Vladimir S.,Sosnovskikh, Vyacheslav Y.
, p. 1764 - 1767 (2016/05/19)
Nonstabilized azomethine ylides are easily trapped by anthraquinone to form stable spiro-oxazolidines, which have an unusual ability to undergo a cycloreversion in the presence of other dipolarophiles at 120-150°C. All tested recycloadditions with carbonyl compounds and electron-poor alkenes occurred in moderate to high yields (41-92%). Moreover, increasing the reaction temperature to 210°C made it possible to obtain adducts with low reactive dipolarophiles.
1,3-Dipolar cycloaddition of unstabilised azomethine ylides by Lewis base catalysis
Pandiancherri, Shveta,Ryan, Sarah J.,Lupton, David W.
, p. 7903 - 7911 (2013/07/05)
Lewis base catalysed 1,3-dipolar cycloaddition between α,β- unsaturated acyl fluorides and N-[(trimethylsilyl)methyl]amino ethers has been achieved using 1 mol% DMAP. Competition experiments and 19F-NMR studies indicate that the cycloaddition o
Pyrrolidine-carboxamides and oxadiazoles as potent hNK1 antagonists
Young, Jonathan R.,Eid, Ronsar,Turner, Cherilyn,DeVita, Robert J.,Kurtz, Marc M.,Tsao, Kwei-Lan C.,Chicchi, Gary G.,Wheeldon, Alan,Carlson, Emma,Mills, Sander G.
, p. 5310 - 5315 (2008/03/11)
The preparation and structure-activity-relationships of novel pyrrolidine-carboxamides and oxadiazoles are described. Compounds in this series were found to be potent hNK1 antagonists in vitro and efficacious in vivo with minimal interactions with P450 liver enzymes. Oxadiazole analog 22 was determined to have excellent hNK1 binding affinity, functional activity, and a good PD response in vivo.
The convenient synthesis of 3-alkyloxycarbonylpyrrolidine derivatives
Dong, Jingchao,Kou, Binbin,Li, Runtao,Cheng, Tieming
, p. 935 - 939 (2007/10/03)
A series of 3-alkyloxycarbonylpyrrolidine derivatives are readily achieved via 1,3-dipolar cycloaddition of α,β-unsaturated esters with nonstabilized azomethine ylides in the presence of samarium diiodide.
1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists. Part 1: Discovery of the pyrrolidine scaffold and determination of its stereochemical requirements
Hale, Jeffrey J.,Budhu, Richard J.,Mills, Sander G.,MacCoss, Malcolm,Malkowitz, Lorraine,Siciliano, Salvatore,Gould, Sandra L.,DeMartino, Julie A.,Springer, Martin S.
, p. 1437 - 1440 (2007/10/03)
A series of 1,3,4-trisubstituted pyrrolidines was discovered to have the ability to displace [125I]-MIP-1α from the CCR5 receptor expressed on Chinese hamster ovary (CHO) cell membranes. CCR5 activity was found to be dependent on the regiochemi
Pyrrolidine and piperidine modulators of chemokine receptor activity
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, (2008/06/13)
The present invention is directed to pyrrolidine and piperidine compounds of the formula I: (wherein R1, R2, R3, R4a, R4b, R4c, R4d, R4e, R4f, R4g, R4h, m, n, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-1, CCR-2, CCR-2A, CCR-2B, CCR-3, CCR-4, CCR-5, CXCR-3, and/or CXCR-4.
Sequential two-electron oxidation of α,α′-disilylmethylamines to generate non-stabilized azomethine ylide: An ideal approach for the construction of substituted and fused pyrrolidine ring systems
Pandey, Ganesh,Lakshmaiah,Gadre, Smita R.
, p. 91 - 98 (2007/10/03)
α,α′-Di(trimethylsilylmethyl)amines undergo sequential double desilylation processes, by two-electron oxidation initiated either by photoinduced electron transfer (PET) or Ag(I)F, to produce non-stabilized azomethine ylides efficiently which upon trapping with appropriate dipolarophiles give the corresponding pyrrolidines. Application of this strategy to cyclic analogue for the rapid construction of biologically important 1-azabicyclo[m,3.0]alkane framework is discussed.
A New and Efficient Strategy for Non-stabilized Azomethine Ylide via Photoinduced Electron Transfer (PET) Initiated Sequential Double Desilylation
Pandey, Ganesh,Lakshmaiah, G.,Kumaraswamy, G.
, p. 1313 - 1314 (2007/10/02)
A practical approach for generating non-stabilized azomethine ylide by PTE initiation is generated.
Parent and N-substitued azomethine ylides from α-amino acids and formaldehyde. An easy access to 2,5-unsubstituted pyrrolidines. Evidence for oxazolidin-5-ones as direct precursor of these reactive intermediates
Joucla, Marc,Mortier, Jacques
, p. 579 - 583 (2007/10/02)
Formaldehyde reacts with α-amino acids and electron deficient alkenes to produce pyrrolidines.Azomethine ylides involved as intermediates in these reactions have been generated from isolated oxazolidin-5-ones which can be considered as the direct precursors of these ylides.
Synthetic Application of Cyanoaminosilanes as Azomethine Ylide Equivalents
Padwa, Albert,Chen, Yon-Yih,Dent, William,Nimmesgern, Hildegard
, p. 4006 - 4014 (2007/10/02)
A series of α-cyanoaminosilanes have been found to act as azomethine ylide equivalents.Treatment of these compounds with silver fluoride in the presence of electron-dificient alkynes and olefins gives substituted pyrroles and pyrrolidines in high yield.It was found that N-benzyl-N-(cyanomethyl)-N-amine undergoes stereospecific cycloaddition with dimethyl fumarate and maleate.The stereospecificity of the reaction is consistent with a concerted cycloaddition reaction.The cycloaddition behavior of an unsymmetrically substituted α-cyanosilylamine with methyl propiolate was also examined and found to react with high overall regioselectivity.The synthetic utility of cyanoaminosilanes as azomethine ylide equivalents was demonstrated by the preparation of a Reniera isoindole alkaloid.The key step in the synthesis involved the reaction of 2-methyl-3-methoxyquinone with N-methyl-N-(cyanomethyl)-N-amine in the presence of silver fluoride to give 2,5-dimethyl-6-methoxy-2H-isoindole-4,7-dione in good yield.
