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Synthesis 2020; 52(10): 1489-1497
DOI: 10.1055/s-0039-1691733
DOI: 10.1055/s-0039-1691733
paper
Electrophilic ipso-Halocyclization of N-Phenyl-N-triflylpropiolamides Leading to 8-Halo-1-azaspiro[4.5]deca-3,6,9-trien-2-ones
This 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)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691733.
- Supporting Information
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