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Synthesis 2023; 55(21): 3610-3616
DOI: 10.1055/a-2114-5426
DOI: 10.1055/a-2114-5426
special topic
C–H Bond Functionalization of Heterocycles
Sustainable Ru(II)-Catalyzed ortho-C(sp2)–H Hydroxyalkylation of Phthalazinones Using Ethyl Glyoxalate: Access to α,α′-Arylcarboxy sec-Alcohols
Fundings from DST-SERB, India (CRG/2021/001143) and the VIT, Vellore (Seed Grant/SG20210167) are gratefully acknowledged.
Abstract
An operationally simple and expeditious protocol for Ru(II)-catalyzed ortho-C(sp2)–H hydroxyalkylation of phthalazinones using commercially available ethyl glyoxalate in 2-Me-THF is reported. This greener approach involves the imine nitrogen on the phthalazinones as a directing group to effect the regioselective hydroxyalkylation. Ample examples of biologically relevant hydroxyalkylated phthalazinones were prepared, and relevant controlled studies were performed to decipher the reaction mechanism.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2114-5426
- Supporting Information
Publication History
Received: 31 March 2023
Accepted after revision: 21 June 2023
Accepted Manuscript online:
21 June 2023
Article published online:
07 August 2023
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