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

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.

Key words

ipso-annulation - ceric ammonium nitrate - propiolamide - dearomatization - aza-spirocycle - benzo-azepinone

Publication History

Received: 19 April 2024

Accepted after revision: 20 June 2024

Accepted Manuscript online:
20 June 2024

Article published online:
15 July 2024

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