55899-13-3Relevant articles and documents
Regioselective Synthesis of Pyrazolo[1,5- a]pyridine via TEMPO-Mediated [3 + 2] Annulation-Aromatization of N-Aminopyridines and α,β-Unsaturated Compounds
Liu, Ya-Zhou,Ma, Xiaofeng,Qiao, Zeen,Shen, Zhongke,Wang, Amu
, (2022/03/01)
A TEMPO-mediated [3 + 2] annulation-aromatization protocol for the preparation of pyrazolo[1,5-a]pyridines from N-aminopyridines and α,β-unsaturated compounds was developed. The procedure offered multisubstituted pyrazolo[1,5-a]pyridines in good to excellent yield with high and predictable regioselectivity. The modification of marketed drugs including Loratadine, Abiraterone, and Metochalcone, and a one-pot three-step gram scale synthesis of key intermediate for the preparation of Selpercatinib were demonstrated. Mechanism studies show that TEMPO serves both as a Lewis acid and as an oxidant.
In Situ Preparation and Consumption of O -Mesitylsulfonylhydroxylamine (MSH) in Continuous Flow for the Amination of Pyridines
Brocklehurst, Cara E.,Koch, Guido,Rothe-P?llet, Stephanie,La Vecchia, Luigi
supporting information, p. 1636 - 1640 (2017/08/11)
The paper demonstrates a safe method in which highly unstable O -mesitylsulfonylhydroxylamine (MSH) can be prepared and consumed in continuous flow. MSH was prepared in situ and used for the flow amination of a range of pyridines, which were subsequently transformed into useful pyrazolopyridine building blocks.
Structure-kinetics relations holding in the amination of six-membered nitrogen-containing heterocyclic compounds
Borodkin,Vorob'ev,Shubin
experimental part, p. 897 - 903 (2011/10/04)
Relative rates of the amination of 3-X- and 4-X-substituted pyridines (X = H, 3-Me, 4-Me, 3-F3C, 3-CN, 4-CN, 3-Cl, 3-Br, 4-MeO, 4-Me 2N), pyrazine, quinoline, isoquinoline, 2,2′- and 4,4′-bipyridines, and 1,10-phenanthroline with O-