54945-11-8Relevant academic research and scientific papers
Development of Scalable Processes for the Preparation of N-Methyl-3-Bromo-5-Methyl Pyrazole
Fox, Richard J.,Markwalter, Chester E.,Lawler, Michael,Zhu, Keming,Albrecht, Jacob,Payack, Joseph,Eastgate, Martin D.
, p. 754 - 762 (2017/05/29)
The development and optimization of two scalable routes to N-methyl-3-bromo-5-methyl pyrazole is described. The initial Sandmeyer route entailed a three-step sequence from crotonitrile and methyl hydrazine, proceeding through the 3-amino pyrazole intermediate. Due to the GTI liability of the 3-amino pyrazole intermediate, a tedious steam-distillation, and 30% overall yield, we developed a second-generation Sandmeyer-free approach from methyl crotonate and methyl hydrazine which leveraged a condensation, bromination, and oxidation sequence. Process development led to the improved preparation of N-methyl-3-bromo-5-methyl pyrazole with increased efficiency and overall yield. The isolation, handling, and storage of the final product was greatly improved through the generation of the triflic acid salt, and salt form studies are also discussed.
Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions
Gould, Eoin,Lebl, Tomas,Slawin, Alexandra M.Z.,Reid, Mark,Smith, Andrew D.
experimental part, p. 8992 - 9008 (2011/01/04)
A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium-ion promoted Diels-Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing
