One-Step Synthesis of Functionalized Pyrazolo[3,4- b ]pyridines via Ring Opening of the Pyrrolinium Ion.

Autor: Rizbayeva TS; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Smolobochkin AV; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Gazizov AS; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Voronina JK; N.S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky prosp. 31, Moscow 119991, Russian Federation., Syakaev VV; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Gerasimova DP; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Lodochnikova OA; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Efimov SV; Kazan Federal University, Kremlyovskaya Str.18, Kazan 420008, Russian Federation., Klochkov VV; Kazan Federal University, Kremlyovskaya Str.18, Kazan 420008, Russian Federation., Burilov AR; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation., Pudovik MA; Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Science, Arbuzova str. 8, Kazan 420088, Russian Federation.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2023 Aug 18; Vol. 88 (16), pp. 11855-11866. Date of Electronic Publication: 2023 Aug 07.
DOI: 10.1021/acs.joc.3c01138
Abstrakt: Herein, we report a highly regioselective one-pot synthesis of pyrazolo[3,4- b ]pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazoles. The reaction proceeds through the sequential nucleophilic addition/electrophilic substitution/C-N bond cleavage and provides easy access to pyrazolo[3,4- b ]pyridine derivatives featuring a primary amino group. Moreover, the reaction can be terminated at the electrophilic substitution stage, thus providing convenient entry to the hardly accessible pyrazolopyrrolopyridine scaffold.
Databáze: MEDLINE