Premium
Regioselective lithiation of 1‐benzylpyrazole derivatives: Synthesis of amides derived from pyrazole
Author(s) -
Górska Agnieszka,
Kliś Tomasz,
Serwatowski Janusz
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4027
Subject(s) - lithium diisopropylamide , chemistry , regioselectivity , pyrazole , deprotonation , tetrahydrofuran , silanes , hydrolysis , lithium (medication) , organic chemistry , medicinal chemistry , silane , catalysis , solvent , medicine , ion , endocrinology
A series of brominated 1‐benzylpyrazoles were deprotonated at the pyrazole 5‐position or the benzylic position on treatment with lithium diisopropylamide in tetrahydrofuran at low temperature. The obtained organolithium intermediates were subjected to reaction with Me 3 SiCl, t ‐BuNCO, ClCONEt 2 or ClCON( i ‐Pr) 2 affording the respective silanes or amides after hydrolysis.