1134-81-2Relevant articles and documents
Atom Transfer Radical Polymerization-Inspired Room Temperature (sp3)C-N Coupling
Coote, Michelle L.,Fung, Alfred. K. K.,Sherburn, Michael S.,Yu, Li-Juan
, p. 9723 - 9732 (2021/07/20)
A simple nonphotochemical procedure is reported for Cu(I)-catalyzed C-N coupling of aliphatic halides with amines and amides. The process is loosely based on the Goldberg reaction but takes place readily at room temperature. It uses Cu(I)Br, a commonly used and inexpensive atom transfer radical polymerization precatalyst, along with the cheap ligand N,N,N′,N″,N″-pentamethyldiethylenetriamine, to activate the R-X bond of the substrate via inner-sphere electron transfer. The procedure brings about productive C-N bond formation between a range of alkyl halide substrates with heterocyclic aromatic amines and amides. The mechanism of the coupling step, which was elucidated through application of computational methods, proceeds via a unique Cu(I) → Cu(II) → Cu(III) → Cu(I) catalytic cycle, involving (a) inner-sphere electron transfer from Cu(I) to the alkyl halide to generate the alkyl radical; (b) successive coordination of the N-nucleophile and the radical to Cu(II); and finally reductive elimination. In the absence of a nucleophile, debrominative homocoupling of the alkyl halide occurs. Control experiments rule out SN-type mechanisms for C-N bond formation.
SUBSTITUTED 6-(1H-PYRAZOL-1-YL)PYRIMIDIN-4-AMINE DERIVATIVES AND USES THEREOF
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Page/Page column 318-319, (2018/04/27)
The present invention covers substituted 6-(1H-pyrazol-1-yl)pyrimidin-4-amine compounds of general formula (I) as described and defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular for the treatment and/or prophylaxis of cardiovascular and renal diseases, as a sole agent or in combination with other active ingredients.
2 (Oxa) as a heterogeneous recyclable catalyst: Synthesis of pyrazoles under mild reaction conditions
Katla, Ramesh,Chowrasia, Rakhi,Manjari, Padma S.,Da Silva, Caren D. G.,Dos Santos, Beatriz F.,Domingues, Nelson L. C.
supporting information, p. 9471 - 9476 (2016/11/11)
We developed a novel and highly efficient protocol for the synthesis of important pyrazole derivatives by using some 1,3-dicarbonyl compounds and phenyl hydrazines via a one-pot protocol. As a recyclable heterogeneous catalyst, we used [Ce(l-Pro)2]2 (Oxa). In addition, the catalyst is recyclable, the proline is economically viable and readily available in both enantiomeric forms and the catalyst is insoluble in almost all solvents and may be easily filtered off from the reaction medium. Moreover, this new synthetic protocol features high conversion, short reaction times, a straightforward procedure and cleaner reaction profiles.
