An efficient TMSOTf-promoted selective triple consecutive insertions of tert-butyl isocyanide into aldehydes has been developed, affording pharmacological interesting 4-cyanooxazoles in high yields in a one pot manner. The given method encompasses a wide range of substrates with tert-butyl isocyanide serving as sources of critical "CN" and "C-N═C" moieties. The versatile transformations of the resulting 4-cyanooxazoles were demonstrated. The key reaction intermediates for plausible mechanisms were determined.

This study developed a one-pot method for synthesis of pharmacologically interesting 4-cyanooxazoles in high yields using tert-butyl isocyanide, offering potential for diverse transformations and applications.

Paper

Triple-Consecutive Isocyanide Insertions with Aldehydes: Synthesis of 4-Cyanooxazoles.

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