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Synthesis 2020; 52(10): 1489-1497
DOI: 10.1055/s-0039-1691733
paper
© Georg Thieme Verlag Stuttgart · New York

Electrophilic ipso-Halocyclization of N-Phenyl-N-triflylpropiolamides Leading to 8-Halo-1-azaspiro[4.5]deca-3,6,9-trien-2-ones

Vito A. Fiore
,
Michael Keim
,
Roland Werz
,
Gerhard Maas  ∗
Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany   Email: gerhard.maas@uni-ulm.de
› Author AffiliationsThis work was supported by the University of Ulm.
Further Information

Publication History

Received: 06 January 2020

Accepted after revision: 31 January 2020

Publication Date:
19 February 2020 (online)

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Abstract

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.

Key words

electrophilic addition - propiolamides - γ-lactams - spiro compounds - triflylamides

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691733.
  • Supporting Information
 

  • References


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