A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

• Li Liu,
• Yue Li,
• Tiao Huang,
• Dulin Kong and
• Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

• disclosed the application of N-fluorobenzenesulfonimide (NFSI) and NBS (N-bromosuccinimide), respectively, as the halogen sources, with diazoacetamide under catalyst-free conditions via a carbene pathway, which constructed 3-fluorooxindoles and 3-bromooxindoles (Scheme 1, reaction 1) [20][21]. Then, the

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

• Lukáš Marek,
• Lukáš Kolman,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

• -[amino(phenyl/methyl)methylidene]-1,3-dihydro-2H-indol-2-ones starting from easily available 3-bromooxindoles or (2-oxoindolin-3-yl)triflate and thioacetamides or thiobenzamides is described. A series of 49 compounds, several of which have previously been shown to possess significant tyrosin kinase

• of all products was confirmed by NMR techniques. Keywords: 3-bromooxindoles; Eschenmoser coupling reaction; thioamides; tyrosin kinase inhibitors; (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones; Introduction 3-(Aminomethylidene)-1,3-dihydro-2H-indol-2-ones (3-(aminomethylidene

• complete decomposition giving mainly the isoindigo derivatives 9a–e. Similar issues were observed when the secondary or tertiary thiobenzamides 3a–i or 4a–c were used. The following Scheme 2 summarizes the main possible reaction routes starting from 3-bromooxindoles 1a–e and various primary, secondary, and