4,5-Dihydro-2<i>H</i>-pyridazin-3-ones as a Platform for the Construction of Chiral 4,4-Disubstituted-dihydropyridazin-3-ones.

ABSTRACT: 4,5-Dihydro-2H-pyridazin-3-ones (DHPDOs) are important synthetic as well as naturally occurring heterocycles. We herein report the synthesis of various 4-monofunctionalized 4,5-dihydro-2H-pyridazin-3-ones and their use as starting materials to access 4,4-disubstituted dihydropyridazin-3-ones in an asymmetric fashion. By using chiral ammonium salt phase-transfer catalysts, conjugate additions of these scaffolds to classical acrylate-based Michael acceptors, as well as quinone methides, can be carried out with moderate to good enantioselectivities and in reasonable yields, affording a new pathway to dihydropyridazin-3-one derivatives with an all-carbon stereocenter.

SUBMITTER: Henry PJ 

PROVIDER: S-EPMC12786495 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature