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

Marc Miller; Johannes C. Vogel; William Tsang; Andrew Merrit; David J. Procter

doi:10.1039/b816608k

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

Marc Miller, Johannes C. Vogel, William Tsang, Andrew Merrit, David J. Procter

Research output: Contribution to journal › Article › peer-review

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. © The Royal Society of Chemistry 2009.

Original language	English
Pages (from-to)	589-597
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	7
Issue number	3
DOIs	https://doi.org/10.1039/b816608k
Publication status	Published - 2009

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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. {\textcopyright} The Royal Society of Chemistry 2009.",

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AU - Miller, Marc

AU - Vogel, Johannes C.

AU - Tsang, William

AU - Merrit, Andrew

AU - Procter, David J.

PY - 2009

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N2 - 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. © The Royal Society of Chemistry 2009.

AB - 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. © The Royal Society of Chemistry 2009.

U2 - 10.1039/b816608k

DO - 10.1039/b816608k

M3 - Article

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JF - Organic and Biomolecular Chemistry

IS - 3

ER -

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

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