38079-40-2Relevant articles and documents
Cascade Synthesis of Kinase-Privileged 3-Aminoindazoles via Intramolecular N-N Bond Formation
Zhu, W. Felix,Kr?mer, Andreas,Knapp, Stefan,Proschak, Ewgenij,Hernandez-Olmos, Victor
, p. 3856 - 3862 (2022/03/02)
3-Aminoindazoles are privileged scaffolds for bioactive drug-like molecules. In this study, a microwave-assisted cascade reaction for the synthesis of N-1 substituted 3-aminoindazoles with yields up to 81% has been developed. Starting from 3-(2-bromoaryl)-1,2,4-oxadiazol-5(4H)-ones, the reaction exhibits a broad substrate scope including anilines, aliphatic amines, and sulfonamides and bypasses selectivity issues between N-1 and 3-amino group. Furthermore, the Differential Scanning Fluorimetry screen of a kinase panel demonstrated the value of targeting N-1 substituted 3-aminoindazoles as kinase-biased fragments.
Method for preparing substituted 3-aminoindazole compound in one step
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Paragraph 0023-0027; 0116-0119, (2020/07/28)
The invention discloses a method for preparing a substituted 3-aminoindazole compound in one step, and belongs to the technical field of organic chemical synthesis. According to the method, simple nitrile and hydrazine compounds are adopted as initial raw
C4-C5 fused pyrazol-3-amines: When the degree of unsaturation and electronic characteristics of the fused ring controls regioselectivity in Ullmann and acylation reactions
Borrell, José I.,Bou-Petit, Elisabeth,Estrada-Tejedor, Roger,Font-Bardia, Mercè,Plans, Arnau,Puigjaner, Cristina,Ramon Y Cajal, Santiago,Rodríguez-Picazo, Nieves,Teixidó, Jordi,Torres-Coll, Antoni
, p. 5145 - 5156 (2020/07/23)
Pyrazol-3-amine is a scaffold present in a large number of compounds with a wide range of biological activities and, in many cases, the heterocycle is C4-C5 fused to a second ring. Among the different reactions used for the decoration of the pyrazole ring, Ullmann and acylation have been widely applied. However, there is some confusion in the literature regarding the regioselectivity of such reactions (substitution at N1 or N2 of the pyrazole ring) and no predictive rule has been so far established. As a part of our work on 3-amino-pyrazolo[3,4-b]pyridones 13, we have studied the regioselectivity of such reactions in different C4-C5 fused pyrazol-3-amines. As a rule of thumb, the Ullmann and acylation reactions take place, predominantly, at the NH and non-protonated nitrogen atom of the pyrazole ring respectively, of the most stable initial tautomer (1H- or 2H-pyrazole), which can be easily predicted by using DFT calculations. This journal is