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Updated: Sep 20, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Synthesis of Trisubstituted Oxazoles via Aryne Induced [2,3] Sigmatropic Rearrangement-Annulation Cascade
Rahul N Gaykar1, Shiksha Deswal1, Avishek Guin1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore-560012, India.
Abstract:
A transition-metal-free, [2,3] sigmatropic rearrangement-annulation cascade of 2-substituted thio/amino acetonitriles with arynes allowing the synthesis of 2,4,5-trisubstituted oxazoles under mild conditions has been demonstrated. The key sulfur/nitrogen ylides were generated by the initial S/N arylation followed by proton transfer, which was followed by the selective [2,3] sigmatropic rearrangement involving the -CN moiety and a subsequent annulation to afford the desired products in reasonable yields.
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