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摘要
9-Fluorenylmethoxycarbonyl was a good protecting group in the field of chemical industry. In the present paper, a new approach for the synthesis of oxadiazine insecticides indoxacarb used 9-fluorenylmethoxycarbonyl as protected group, and triphosgene for chloroformylation. A convenient synthesis of 9-fluorenylmethoxycarbonylhydrazine can be achieved by the nucleophilic substitution reaction of 9-fluorenylmethyl chloroformate and hydrazine hydrate. 4a-Methyl-2-(9-fluorenylmethyl)-7-chloro-indeno [1,2e][1,3,4] oxadia zine-2,4a (3H,5H)-dicarboxylate can be produced via ketone -hydrazine crosslink reaction and cyclization. A preparation of carbamic acid-(chlorocarbonyl)-[(4-trifluoromethoxy) phenyl] me ester can be obtained by the chloroformylation of triphosgene. Finally, the deprotection of 9-fluorenylmethoxy carbonyl and condensation with carbamic acid-(chlorocarbonyl)-[(4-trifluoromethoxy) phenyl] me ester can afford indoxacarb in good yield. A new method for the synthesis of oxadiazine insecticides indoxacarb used 9-fluorenylmethoxycarbonyl-protected group to produce 9-fluorenylmethoxycarbonylhydrazine, then through the ketone-hydrazine crosslink reaction, cyclization, deprotection, chloroformylation, and condensation in good yield.
- 出版日期2016-9
- 单位常州大学
