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Synthesis 2006(6): 995-998
DOI: 10.1055/s-2006-926365
DOI: 10.1055/s-2006-926365
PAPER
© Georg Thieme Verlag Stuttgart · New York
The Triphenyl Phosphite-Chlorine Reagent in the Synthesis of Pyrroles from N-Allylamides
Further Information
Received
6 September 2005
Publication Date:
27 February 2006 (online)
Publication History
Publication Date:
27 February 2006 (online)
Abstract
A novel application of (PhO)3P-Cl2 chemistry to the synthesis of 2-substituted and 2,3-disubstituted pyrroles from N-allylamides is illustrated. A mild procedure is used to generate the imino chloride intermediates, which are subsequently cyclized to pyrroles. The products are smoothly obtained in moderate to good overall yields.
Key words
triphenyl phosphite - chlorine - pyrroles - allylamides - cyclizations
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References
While triphenyl phosphate originated as a by-product of the halogenation step, [6a] transesterification of triphenyl phosphate during the base-promoted cyclization would furnish phenol.