Study On Synthesis Of Substituted O-Bromophenylacetylene And The Application In The Synthesis Of Substituted Indoline

The thesis has made collective reviews on the application and synthetic methods of substituted o-bromophenylacetylenes,as well as the application and synthetic methods of indolines, which were based on the comprehensive study of related domestic and abroad articles. A novel two-step synthesis of substituted o-bromophenylacetylenes from o-bromostyrenes has been successfully developed. Catalyzed by iodide copper, substituted indolines could be abtained from o-bromophenyl- acetylenes participated one-pot multicomponent reactions.Used as raw materials, substituted o-bromostyrenes treated with bromine could quantitively afford corresponding addition products in CCl4 solvent at room temperature. Substituted o-bromophenyl- acteylenes could be abtained in high yields when the addition products were treated with three equivalents of potassium tert-butoxide in dry THF at room temperature. Our procedure has some advantages, such as readily available raw materials, mild reaction condition, ease of operation, and high yields.Catalyzed by iodide copper, the three-component reactions of o-bromophenylacteylenes, sulfonyl azides, and primary amines readily occurred. To the reaction solution were then added iodide copper, L-proline, and two equivalents of potassium carbonate. The substituted indoline products could be abtained after the mixtures were stired under 60℃under N2 for 2 h. Our procedure has some advantages, such as reaction generality, mild reaction condition, and high convergency.