Synthesis of Heterocyclic-fused Imidazoles by Pyrolysis of N-Heterocyclic Isoxazol-5(2H)-ones
Steven-Alan G. Abel A , Mathew O. Eglinton A , James K. Howard A , Dylan J. Hunt A , Rolf H. Prager B and Jason A. Smith A C
+ Author Affiliations
- Author Affiliations
A School of Physical Sciences-Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia
B School of Chemical and Physical Sciences, Flinders University, Adelaide, SA 5001, Australia
C Corresponding author. Email: Jason.Smith@utas.edu.au
Australian Journal of Chemistry 67(9) 1228-1233 https://doi.org/10.1071/CH14119
Submitted: 6 March 2014 Accepted: 28 March 2014 Published: 19 May 2014
Abstract
The synthesis of heterocyclic-fused imidazoles was achieved by flash vacuum pyrolysis (FVP) of N-heterocyclic isoxazol-5(2H)-ones via an iminocarbene intermediate. Unlike iminocarbenes generated from triazoles, no structural rearrangements were observed during the current synthesis method. We also demonstrated that less volatile isoxazol-5(2H)-one derivatives yield the corresponding imidazoles by condensed phase pyrolysis.
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