97754-27-3Relevant academic research and scientific papers
Isoindolinone Synthesis: Selective Dioxane-Mediated Aerobic Oxidation of Isoindolines
Thapa, Pawan,Corral, Esai,Sardar, Sinjinee,Pierce, Brad S.,Foss, Frank W.
, p. 1025 - 1034 (2019)
N-Alkyl and N-aryl-isoindolinones were prepared by a dioxane-mediated oxidation of isoindoline precursors. The transformation exhibits unique chemoselectivity for isoindonlines. A chiral tertiary (3°)-benzylic position was not racemized during oxidation, and methyl indoprofen was prepared by late stage oxidation. Mechanistic studies suggest a selective H atom transfer, which avoids many known oxidation (by-)products of isoindolinones.
Oxidative Desymmetrization of Isoindolines Realized by tert -Butyl Nitrite (TBN) Initiated Radical sp 3C-H Activation Relay (CHAR)
Sun, Zheng,Shao, Yu,Zhang, Shuwei,Zhang, Yuxian,Yuan, Yu,Jia, Xiaodong
, p. 1663 - 1671 (2021/02/01)
An oxidative desymmetrization of isoindolines was realized by TBN initiated radical sp 3C-H activation relay (CHAR), providing a series of ω-hydroxylactams in high yields. This reaction exhibits broad substrate scope and functional group tolerance, and even N -alkyl iso-indolines can be well tolerated. The mechanistic study shows that the C-H bond oxidation, dioxygen trapping and intramolecular 1,5-H shift might be the key steps to achieve the oxidative desymmetrization.
Intramolecular C(sp3)-N coupling by oxidation of benzylic C,N-dianions
Jeffrey, Jenna L.,Bartlett, Emily S.,Sarpong, Richmond
, p. 2194 - 2197 (2013/03/28)
What a couple! An intramolecular, C(sp3)-N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural produc
An efficient method for the synthesis of 2, 3-dihydro-lH-isoindoles
Subbarayappa, Adimurthy,Patoliya, Paresh U.
experimental part, p. 545 - 552 (2009/12/06)
The synthesis of Af-substituted 2, 3-dihydro-lH-isoindoles from α, α'-dibromo-o-xylene and various primary amines in basic medium under ambient conditions is described. Especially the selection of 1, 4-dioxane as solvent and sodium hydroxide as suitable base to maintain the homogeneity of the medium are key steps to promote the reaction efficiently. Primary alkyl amines react faster as compared to their aromatic analogues under the conditions studied. Irrespective of the starting amine used, all the reactions proceed smoothly and provide 2, 3-dihydro-lH-isoindoles derivatives in excellent yields compared to hitherto known methods.
