73502-03-1Relevant articles and documents
Palladium-Catalyzed Tandem Carbonylative Diels-Alder Reaction for Construction of Bridged Polycyclic Skeletons
Wang, Siyuan,Zhou, Yangkun,Huang, Hanmin
supporting information, p. 2125 - 2129 (2021/04/05)
A palladium-catalyzed tandem carbonylative lactonization and Diels-Alder cycloaddition reaction between aldehyde-tethered benzylhalides and alkenes has been developed. A range of alkenes and aldehyde-tethered benzylhalides bearing different substituents can be successfully transformed into the corresponding bridged polycyclic compounds in good yields. This strategy provides a unique approach to complex lactone-containing bridged polycyclic compounds.
Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate
Lai, Huifang,Lin, Jin,Xu, Jiexin,Zha, Daijun
supporting information, p. 7621 - 7626 (2021/09/22)
Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, we describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Additionally, the reaction mechanism appears to involve a radical and a carbocationic pathway.
Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
supporting information, p. 224 - 239 (2017/12/08)
One approach for the synthesis of isoindolinones, a privileged bioactive heterocyclic core structure, involves a condensation reaction of o-phthaldialdehydes with a suitable nitrogen-containing nucleophile. This fascinating reaction is revisited here in the context of the use of o-phthaldialdehydes that contain additional substituents in the aromatic ring leading to a detailed analysis of the regioselectivity of the reaction. Eleven monosubstituted o-phthaldialdehydes were synthesised and reacted with alanine. The regioselectivity observed across the eleven substrates led to the design of a disubstituted substrate that reacted with very high control. A gram-scale reaction followed by esterification gave one major regioisomer in high yield. In addition, the regioselectivity observed on reaction of two novel monodeuterated substrates led to an increased mechanistic understanding.