Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones

Synthesis Pub Date : 2024-07-15 DOI:10.1055/a-2349-6736
Chada Raji Reddy, Thallamapuram Nagendraprasad, Jannatul Islam, Uprety Ajaykumar, Cirandur Suresh Reddy, Srivari Chandrasekhar
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Abstract

Iodine-mediated oxidative annulations of N-benzyl-propiolamides are disclosed for the first time, providing either azaspiro[5.5]undecatrienones via dearomative ipso-annulation or benzo[c]azepinones through ortho-annulation. The selective construction of the aforementioned products is based on the ceric ammonium nitrate (CAN)-promoted divergent reactivity of the propiolamide, directed by the substituents on the phenyl ring of the N-benzyl group.

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N-Benzyl-propiolamides 的碘化制备,生成氮杂螺[5.5]十一烷三烯酮或苯并[c]氮杂卓酮
首次公开了碘介导的 N-苄基丙炔酰胺氧化环化反应,通过脱芳基异环化反应提供氮杂螺[5.5]十一烷三烯酮,或通过正环化反应提供苯并[c]氮杂环庚酮。上述产品的选择性构建是基于硝酸铈铵(CAN)促进的丙炔酰胺的发散反应性,由 N-苄基苯环上的取代基引导。
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