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Electrophilic ipso-Halocyclization of N-Phenyl-N-triflylpropiolamides Leading to 8-Halo-1-azaspiro[4.5]deca-3,6,9-trien-2-ones
Synthesis ( IF 2.6 ) Pub Date : 2020-02-19 , DOI: 10.1055/s-0039-1691733
Gerhard Maas 1 , Vito A. Fiore , Michael Keim , Roland Werz
Affiliation  

N-Phenyl-N-triflylpropiolamides react with iodine chloride or iodine bromide by an intramolecular electrophilic ipso-halocyclization/nucleophilic halide addition sequence to furnish cyclohexadiene-spiro-γ-lactams. These products can undergo cleavage of the amide bond with primary amines and of the N–Cspiro bond with secondary amines, leading to N-alkyl-2-iodo-3-phenylacrylamides and N-(4-halophenyl)-2-iodo-3-(2-triflylamino)phenylacrylamides, respectively.

中文翻译:

N-苯基-N-三氟乙丙酰胺的亲电ipso-卤代化,导致8-Halo-1-azaspiro [4.5] deca-3,6,9-trien-2-ones

Ñ苯基Ñ -triflylpropiolamides与氯化碘或碘溴化物通过分子内反应电本位-halocyclization /亲核加成卤化物序列配料环己二烯-螺- γ-内酰胺。这些产物可能会与伯胺发生酰胺键断裂,而与仲胺发生N–C键断裂,从而生成N-烷基-2-碘-3-苯基丙烯酰胺和N-(4-卤代苯基)-2-碘- 3-(2-三氟氨基)苯基丙烯酰胺。
更新日期:2020-04-21
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