Synthesis of Fused [5,5]‐1,2,4‐Triazoles via Tandem Thioimidate Cyclopropane Rearrangement–Cyclization

Abstract

The synthesis of fused [5,5]‐1,2,4‐triazoles via a tandem cyclopropane rearrangement–cyclization sequence is described. Optimization of the cyclization reaction was achieved thermally using iPrOH as the solvent in the presence of TEA. This method was applied to the preparation of 3‐substituted‐7‐aryl‐pyrrolo‐1,2,4‐triazoles in good to excellent yields.

Keywords:

• Cyclizations
• cyclopropane
• fused‐ring systems
• rearrangements
• triazoles

Acknowledgment

The authors thank S. N. Pitzenberger and S. Vargas for NMR determinations and M. G. Bock for helpful discussions and support.