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

• University, Haikou 571199, Hainan Province, P. R. China 10.3762/bjoc.17.150 Abstract A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate

• -substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability. Keywords: acidolysis; haloid acids; isatin; 3-monohalooxindole; 3-phosphate

• challenge in chemistry. In order to achieve this goal, and on the basis of our previous experiences in the functionalization of oxindoles [33][34], we herein designed a nucleophilic substitution method of an isatin-derived 3-phosphate-substituted oxindole with haloid acids, leading to 3-monohalooxindoles