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Issue 3, 2009
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Formation of N-heterocycles by the reaction of thiols with glyoxamides: exploring a connective Pummerer-type cyclisation

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Abstract

The reaction of thiols with glyoxamides provides a convenient method for the generation of thionium ions and the initiation of Pummerer-type reactions. When the glyoxamides contain tethered aromatic nucleophiles, N-heterocycles are formed by a thionium ion cyclisation. The scope and mechanism of the connective Pummerer-type process has been investigated using a range of thiols, Lewis acids and both mono- and bis-glyoxamides. The utility of the process has been illustrated in a synthesis of the indoloquinoline natural product, neocryptolepine.

Graphical abstract: Formation of N-heterocycles by the reaction of thiols with glyoxamides: exploring a connective Pummerer-type cyclisation

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Supplementary files

Article information


Submitted
22 Sep 2008
Accepted
31 Oct 2008
First published
12 Dec 2008

Org. Biomol. Chem., 2009,7, 589-597
Article type
Paper

Formation of N-heterocycles by the reaction of thiols with glyoxamides: exploring a connective Pummerer-type cyclisation

M. Miller, J. C. Vogel, W. Tsang, A. Merrit and D. J. Procter, Org. Biomol. Chem., 2009, 7, 589
DOI: 10.1039/B816608K

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