A convenient synthesis of 2-alkyl-3-aryl-2, 3-dihydro-1H-isoindol-1-ones by the reaction of N-alkyl-N-[(2-bromophenyl)methyl]benzamides with butyllithium. Issue 33 (18th August 2016)

• Record Type: Journal Article
• Authors: Kobayashi, Kazuhiro; Chikazawa, Yuuki
• Is Part Of: Tetrahedron. Volume 72:Issue 33(2016)
• Page Start: 5100
• Page End: 5105
• Publication Date: 2016-08-18
• Subjects: Isoindolinone -- 2, 3-dihydro-1H-isoindol-1-one -- Organolithium -- Bromine/lithium exchange -- Ring closure; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.06.082
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An unprecedented and convenient synthetic approach to 2, 3-dihydro-1 H -isoindol-1-one (isoindolinone) derivatives has been developed. The key and final step of the method is the reaction of N -alkyl- N -( o -bromobenzyl)benzamides with butyllithium in THF at −78 °C. The corresponding 2-alkyl-3-aryl-2, 3-dihydro-1 H -isoindol-1-ones were produced in moderate-to-fair yields, probably via oxidation of the initially formed corresponding 2 H -isoindole derivatives with air during workup. Graphical abstract: