34063-52-0Relevant articles and documents
Scalable, easy synthesis, and efficient isolation of arylnitromethanes: a revival of the Victor Meyer reaction
Alaime, Thibaud,Delots, Audrey,Pasquinet, Eric,Suzenet, Franck,Guillaumet, Gérald
, p. 1337 - 1341 (2017/01/21)
A modified approach to synthesize and isolate arylnitromethanes is described. The method takes advantage of the significant difference in acidity between the arylnitromethane and the major impurity of the reaction, the nitrite ester. The arylnitromethanes resulting from this process are obtained in high yields and are analytically pure, i.e., they do not require distillation or further purification, which is a comfortable improvement of the ancestral Victor Meyer reaction.
Synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones utilizing pyrrole weinreb amides
Greger, Jessica G.,Yoon-Miller, Sarah J. P.,Bechtold, Nathan R.,Flewelling, Scott A.,MacDonald, Jacob P.,Downey, Catherine R.,Cohen, Eric A.,Pelkey, Erin T.
, p. 8203 - 8214 (2011/12/04)
A regiocontrolled synthesis of unsymmetrical 3,4-diaryl-3-pyrrolin-2-ones has been achieved in three steps from 1,2-diaryl-1-nitroethenes with pyrrole-2-carboxamides (pyrrole Weinreb amides) serving as the key linchpin intermediates. Two different methods for the preparation of the requisite nitroalkenes were investigated: (1) modified Henry reaction between arylnitromethanes and arylimines; and (2) Suzuki-Miyaura cross-coupling reaction of 2-aryl-1-bromo-1-nitroethenes with arylboronic acids. Some difficulty was encountered in the preparation of arylnitromethanes, thus leading to the exploration of a cross-coupling strategy that proved more useful. A Barton-Zard pyrrole cyclocondensation reaction between 1,2-diaryl-1-nitroethenes and N-methoxy-N-methyl-2-isocyanoacetamide gave the corresponding pyrrole Weinreb amides, which were then converted into the desired 3-pyrrolin-2-ones in two steps. Overall, this method allowed for the construction of 3,4-diaryl-3- pyrrolin-2-ones with complete regiocontrol of the substituents with respect to the lactam carbonyl. The utility of this synthetic methodology was demonstrated by the preparation of eight unsymmetrical and symmetrical 3,4-diaryl-3-pyrrolin- 2-ones including the N-H lactam analogue of the selective COX-II inhibitor, rofecoxib.
Nucleophilicities of nitroalkyl anions
Bug, Thorsten,Lemek, Tadeusz,Mayr, Herbert
, p. 7565 - 7576 (2007/10/03)
The kinetics of the reactions of eight nitroalkyl anions (nitronate anions) with benzhydrylium ions and quinone methides in DMSO and water were investigated photometrically. The second-order rate constants were found to follow a Ritchie constant selectivi