53606-06-7Relevant articles and documents
SPIRO COMPOUNDS AS GLYCOSIDASE INHIBITORS
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Page/Page column 116, (2020/03/15)
Compounds of formula (I) wherein A, R, L, Z, Q1, Q2 and n have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.
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.
supporting information; experimental part, 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.
Correlation pKa - activitee catalitique des thiols dans la reeaction d'hydrolyse de l'aceetate de p-nitropheenyle
Brembilla, Alain,Roizard, Denis,Schoenleber, Jacqueline,Lochon, Pierre
, p. 2330 - 2336 (2007/10/02)
The kinetic study of the hydrolysis of p-nitrophenylacetate in the presence of primary thiols indicates the thiolate anion as the sole catalytic species.Comparison of the true second order constants (kRS-) reveals that purely aliphatic primary thiols behave differently from aromatic α-substituted primary thiols.In the latter group a correlation can be established between the true second order rate constants and the pKSH values by means of the Broensted equation log kRS- = βpKSH + C, with β equal to 0.40 and C equal to -0.85.