1,2,3-Benzotriazine Synthesis by Heterocyclization of p-Tosylmethyl Isocyanide Derivatives

An efficient methodology to form 4-alkoxy- and 4-aryloxybenzo[d][1,2,3]triazines via an intramolecular heterocyclization of 1-azido-2-[isocyano(p-tosyl)methyl]benzenes under basic conditions has been developed. DFT calculations have been performed to further understand the mechanism of this heterocyclization, which occurs in good to excellent yields with a broad scope.

Automated summary

An efficient methodology has been developed for the synthesis of 4-alkoxy- and 4-aryloxybenzo[d][1,2,3]triazines via an intramolecular heterocyclization of 1-azido-2-[isocyano(p-tosyl)methyl]benzenes under basic conditions. DFT calculations were performed to gain a better understanding of the mechanism behind this heterocyclization, which demonstrated good to excellent yields with a broad scope.