15364-06-4Relevant academic research and scientific papers
Palladium-catalyzed C-H arylation of 2,5-substituted pyrroles
Wagner, Anna M.,Sanford, Melanie S.
, p. 288 - 291 (2011/04/17)
The palladium-catalyzed direct arylation of 2,5-substituted pyrrole derivatives with diaryliodonium salts to generate tri-, tetra-, and penta-substituted pyrrole products is described. The scope and limitations of these transformations are also reported.
Ring expansion of 2-(α-hydroxyalkyl)azetidines: A synthetic route to functionalized pyrrolidines
Durrat, Francois,Sanchez, Monica Vargas,Couty, Francois,Evano, Gwilherm,Marrot, Jerome
experimental part, p. 3286 - 3297 (2009/04/07)
A series of 2-(α-hydroxyalkyl)azetidines synthesized from enantiomerically pure β-amino alcohols and presenting various patterns both on the four-membered ring and on the adjacent hydroxy group were treated with either thionyl chloride or methanesulfonyl chloride in the presence of triethylamine. The thus-prepared 2-(α-chloro- or α- methanesulfonyloxyalkyl) azetidines were shown to rearrange stereospecifically into 3-(chloro- or methanesulfonyloxy)pyrrolidines. When this rearrangement is conducted in the presence of an added nucleophile (NaN3, KCN, KOH, or NaOAc), the produced pyrrolidine incorporates the added nucleophile at C-3 stereospecifically. The relative configuration of the substituents in the formed pyrrolidines is consistent with a mechanism involving the formation of an intermediate bicyclic aziridinium ion, which is opened regioselectively at the bridgehead carbon atom. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
The Reactions of Monoalkylthio- or Monoarylthio-Substituted Cyclopropenium Salt with Nitrogen Nucleophiles: Formation of Polyfunctionally Substituted Pyrroles or Pyrazoles
Yoshida, Hiroshi,Utsumi, Fumitaka,Suzuki, Hideki,Ito, Satoru,Sakashita, Shin-ichi,et al
, p. 698 - 702 (2007/10/02)
The reactions of monoalkylthio- or monoarylthio-substituted cyclopropenium salt (1) with a number of secondary amines were studied.The amines, such as N-methylaniline, yielded indenes, whereas N-alkyl- or N-arylbenzylamines gave 1-alkyl or 1-aryl-2-phenyl
REGIOSELECTIVITY IN THE 1,3-DIPOLAR CYCLOADDITION REACTION OF 3-METHYLOXAZOLIUM 5-OLATES WITH ACETYLENIC DIPOLAROPHILES
Croce, Piero Dalla,Rosa, Concetta La
, p. 2825 - 2832 (2007/10/02)
The cycloaddition reaction of unsymmetrically substituted munchnones with monosubstituted alkynes has been examined.The reaction affords a mixture of regioisomeric pyrroles.The observed regioselectivity is qualitatively discussed on the basis of the MO-pe
OXIDATION OF 1,2,3,4,6,-SUBSTITUTED PYRIDINIUM SALTS WITH FERRICYANIDE
Nesvadba, Petr,Kuthan, Josef
, p. 543 - 548 (2007/10/02)
Quaternary pyridiniun salts IIa-IId are oxidized with alkaline solution of potassium ferricyanide to give a mixture of pyrrole derivatives Ia-Ib and IVa-IVd.The quaternary salt IIeunder the same conditions affords a mixture of compouns IVe and V vhereas I
