197007-02-6Relevant articles and documents
Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions
Redlich, Mark,Hossain, M. Mahmun
, p. 8987 - 8990 (2004)
The synthesis of a series of iron-pybox complexes and their employment in the catalytic asymmetric aziridine forming reaction is presented. When AgSbF6 is used as an initiator, the i-pr- and t-bu-pybox complexes produce 47% of the cis-aziridine
Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines
Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 6452 - 6456 (2019/09/06)
Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.
Pharmaceutical compositions comprising 4-quinolones for treating cancers
-
, (2008/06/13)
A non-cytotoxic pharmaceutical composition acting on the proliferation of clonogenic cells in malignant tumors and including an efficient amount of a compound selected among the compounds of formula (I) and (Ia).
An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate
Mayer, Michael F.,Wang, Qinwei,Hossain, M. Mahmun
, p. 78 - 83 (2007/10/03)
The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines: A highly diastereoselective synthesis of cis-aziridine carboxylates
Sengupta,Mondal
, p. 6245 - 6248 (2007/10/03)
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines give aziridine carboxylates under mild conditions, low catalyst loading and with high cis-selectivity. (C) 2000 Elsevier Science Ltd.
Aziridine synthesis in protic media by using lanthanide triflates as catalysts
Xie, Wenhua,Fang, Jianwen,Li, Jun,Wang, Peng George
, p. 12929 - 12938 (2007/10/03)
Ln(OTf)3-catalyzed aziridine synthesis from imines and diazo compounds was studied in a variety of protic media. The reactions proceeded readily under mild conditions and were highly selective, affording predominantly cis aziridines. The imines used were typically those derived from aromatic aldehydes and aromatic amines, with either electron-donating or electron- withdrawing substituents. N-benzyl aryl aldimines and imines derived from aromatic amines and hindered aliphatic aldehydes were also found to work well. Among the three diazo compounds examined, ethyl diazoacetate (EDA) and 3-nitrophenyl diazomethane were effective reagents for the aziridination. However, the reactions of ethyl diazoacetoacetate failed to give any desired product. Six lanthanides triflates as well as Sc(OTf)3 and Y(OTf)3 were tested as catalyst in the aziridination reaction. The formation of the by- products was also discussed.
Catalytic preparation of aziridines with an iron lewis acid
Mayer, Michael F.,Mahmun Hossain
, p. 6839 - 6844 (2007/10/03)
The iron Lewis acid, [(;75-C5H5)Fe(CO)2(THF)]+[BF4]-) was found to be an effective catalyst for the preparation of aziridines. This new method provides a facile, one-step route to predominantly cisaziridines, with yields up to 95%, from compounds with a diazo functionality and a variety of substituted AT-benzylidene imines with N-aryl or AT-alkyl groups. The reaction mechanism is believed to proceed through an electrophilic iminium ion intermediate. To support this idea, the iron Lewis acid-imine complex [(?75-C5H5)Fe(CO)2(PhCH=NPh)]+[BF.j]- was prepared, characterized, and reacted with different diazo compounds to provide the resultant czs-aziridines. Alternatively, it may be possible that the aziridines were derived from an electrophilic carbenoid intermediate, as is often proposed. Thus, the iron carbene [(2-CsIWFeCCOMCHPhOl+LSOaCFg]- was prepared and treated with AT-benzylideneaniline; however, the resultant aziridine was not formed.
Facile synthesis of aziridines from imines and diazoesters or aldehydes, amines, and diazoesters using a catalytic amount of lanthanide triflate
Nagayama, Satoshi,Kobayashi, Shu
, p. 685 - 686 (2007/10/03)
In the presence of a catalytic amount of lanthanide triflate (Ln(OTf)3), imines reacted with ethyl diazoester in hexane at room temperature to afford the corresponding aziridines in high yields with high diastereoselectivities. Based on these r
