133379-09-6Relevant articles and documents
Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine
D'Hollander, Agathe C.A.,Westwood, Nicholas J.
, 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.
A New Synthetic Route to 4-Bromo-7-methoxyphthalide and 3-Hydroxy-7-methoxyphthalide from 2-Methoxy-6-methylbenzoate Side Chain and Nuclear Bromination
Islam, Md. Rabiul,Joule, John A.
, p. 367 - 378 (2007/10/02)
Ethyl 2-methoxy-6-methylbenzoate was converted via its acid and acid chloride, into the methyl ester.Bromination of the methyl and ethyl esters with the halogen in carbon tetrachloride at reflux in the presence of light resulted in both side-chain and nuc
