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Synthesis
DOI: 10.1055/a-2349-6736
DOI: 10.1055/a-2349-6736
paper
Iodo-Annulations of N-Benzyl-propiolamides Leading To Azaspiro[5.5]undecatrienones or Benzo[c]azepinones
C.R.R. thanks the Science and Engineering Research Board (SERB), New Delhi, for funding (CRG/2021/007367). U.A. and J.S. thank the Department of Science and Technology, New Delhi, for research fellowships (DST-INSPIRE).
![](https://www.thieme-connect.de/media/synthesis/EFirst/lookinside/thumbnails/ss-2024-t0149-op_10-1055_a-2349-6736-1.jpg)
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-azepinoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2349-6736.
- Supporting Information
Publikationsverlauf
Eingereicht: 19. April 2024
Angenommen nach Revision: 20. Juni 2024
Accepted Manuscript online:
20. Juni 2024
Artikel online veröffentlicht:
15. Juli 2024
© 2024. Thieme. All rights reserved
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