Synthesis of N-vinyl isothiocyanates and carbamates by the cleavage of NH-1,2,3-triazoles with one-carbon electrophiles

Metal-free cascade reaction of NH-1,2,3-triazoles with one-carbon electrophiles, such as thiophosgene and triphosgene, led to N-vinylated ring cleavage products. Using this approach the synthesis of N-vinylisothiocyanates from NH-triazoles and thiophosgene was achieved. A variety of multifunctional compounds, such as N-vinylcarbamates, unsymmetrical vinylureas, carbamothioates, etc. was prepared by a one-pot method from NH-triazoles, triphosgene and nucleophiles.

Automated summary

Metal-free cascade reaction of NH-1,2,3-triazoles with one-carbon electrophiles, such as thiophosgene and triphosgene, generates N-vinylated ring cleavage products. N-vinylisothiocyanates can be synthesized from NH-triazoles and thiophosgene using this approach. A variety of multifunctional compounds, such as N-vinylcarbamates, unsymmetrical vinylureas, carbamothioates, etc. were prepared by a one-pot method from NH-triazoles, triphosgene, and nucleophiles.