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Regioselective Construction and Screening of 1,3-Disubstituted Tetrahydroindazolones in Enantiomerically Pure Pairs
In this paper, we describe a regioselective synthetic
pathway for
enantiopure 1,3-disubstituted tetrahydroindazolone derivatives via
the condensation of 2-acylcyclohexane-1,3-dione with various alkyl-
and arylhydrazines using the steric effects of a Boc-protected pyrrolidine
ring. This synthetic method has a broad scope for substrate generality
for various hydrazines with excellent regioselectivity. To maximize
the molecular diversity, further diversifications of 1,3-disubstituted
tetrahydroindazolones were pursued by systematic <i>N</i>-modification of the secondary amine of the pyrrolidine ring using
solution-phase parallel synthesis with polymer-supported reagents.
A library containing a total of 272 drug-like tetrahydroindazolones,
including 85 enantiomeric pairs, was constructed; the average purity,
without further purification, was 95%