Studies on Wallach's imidazole synthesis
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 675-679
- https://doi.org/10.1039/p19930000675
Abstract
The reaction of the N-benzylamides of N-heterocyclic carboxylic acids 3 and 6–9 with phosphorus pentachloride affords heterocondensed imidazoles 4 and 10–14 by a scheme reminiscent of Wallach's imidazole synthesis starting from N.N′-dialkyloxamides. Kinetic and labelling experiments are described which support a mechanism involving nitrite ylide species and allow a better understanding of the Wallach reaction. The limiting parameter for the formation of heteroanellated imidazoles is the electron availability of the heterocyclic ring.Keywords
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