94360-59-5Relevant academic research and scientific papers
A Convenient One-Pot Synthesis of Substituted 1,1-Dicyanocyclopropanes from Sulfonium Salts, Malononitrile, and Carbonyl Compounds
Shestopalov, Aleksandr,Rodinovskaya, Lyudmila,Shestopalov, Anatoliy,Zlotin, Sergey,Nesterov, Vladimir
, p. 2309 - 2312 (2003)
The three-component reaction of sulfonium salts 1, malononitrile 3, and aldehydes 2 in the ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate ([BMIM][PF6]) or in EtOH in the presence of Et3N is a convenient one-pot method for synthesis of substituted 1,1-dicyanocyclopropanes (7 and 9). The reaction of compounds 1-3 occurs stereoselectively to form substituted transcyclopropanes (7), whose structures were confirmed by the data of physicochemical methods, including X-ray diffraction analysis. The yield of cyclopropanes produced by the reaction in the ionic liquid is 8-21% higher than that in EtOH.
Nucleophilicity parameters of pyridinium ylides and their use in mechanistic analyses
Allg?uer, Dominik S.,Mayer, Peter,Mayr, Herbert
supporting information, p. 15216 - 15224 (2013/11/06)
Kinetics of the reactions of pyridinium, isoquinolinium, and quinolinium ylides with diarylcarbenium ions, quinone methides, and arylidene malonates (reference electrophiles) have been studied in dimethylsulfoxide solution by UV-vis spectroscopy. The seco
Stereoselective synthesis of functionalized cyclopropane derivatives via α-thiocyanate ketone-based three-component reaction
Wu, Fei-Yue,Li, Ying,Feng, Hui,Wu, Qiong,Jiang, Bo,Shi, Feng,Tu, Shu-Jiang
experimental part, p. 2459 - 2465 (2011/09/19)
α-Thiocyanate ketone-based three-component reactions have been established for the stereoselective synthesis of functionalized electron-deficient trans-cyclopropanes. The multicomponent reactions were conducted by reacting readily available and inexpensiv
Indium(I) bromide-promoted stereoselective preparation of cyclopropanes via sequential aldol-type coupling/elimination/Michael-induced ring closure reaction from α,α-dichloroacetophenone and aldehydes
Peppe, Clovis,das Chagas, Rafael Pav?o,Burrow, Robert Alan
, p. 3441 - 3445 (2008/12/22)
The indium enolate generated from indium(I) bromide and α,α-dichloroacetophenone reacts with aldehydes to produce (syn + anti)-2-chloro-3-hydroxy-propan-1-ones which can be converted to their trans-prop-2-en-1-ones derivatives upon reaction with an extra equivalent of InBr. The enones undergo Michael-induced ring closure reactions with an extra equivalent of the initial enolate to afford the corresponding cyclopropane derivatives, according to a sequenced reaction mechanism.
CYCLIZATION OF NITRILES. IX. SYNTHESES BASED ON 2-ARYL-3-AROYL-1,1-DICYANOPROPANES
Shestopalov, A. M.,Promonenkov, V. K.,Sharanin, Yu. A.,Rodinovskaya, L. A.,Sharanin, S. Yu.
, p. 1382 - 1401 (2007/10/02)
2-Aryl-3-aroyl-1,1-dicyanopropanes and 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes were synthesized from chalcones and malononitrile and were converted into 4,6-diaryl-2-bromo-3-cyanopyridines and 3-cyano-2(1H)-pyridinethiones.The 2-aryl-3-aroyl-1-bromo-1,1-dicyanopropanes proved convenient intermediates for the production of the corresponding cyclopropanes and other compounds.By their reaction with urea a new method was developed for the production of substituted 3-cyano-2(1H)-pyridinethiones.The 2-bromo-3-cyanopyridines contain a mobile bromine atom readily exchanged for the various nucleophilic residues of alcohols and amines and for iodide, and cyano and thiocyanato groups.The 3-cyano-2(1H)-pyridinethiones were used in the synthesis of 3-aminothienopyridines through the isolated 2-Z-methylthio-3-cyanopyridines.
