Toward the Synthesis of Tetrazino-tetrazine 1,3,6,8-Tetraoxide (TTTO): An Approach to Non-annulated 1,2,3,4-Tetrazine 1,3-Dioxides

摘要

A novel approach for the synthesis of 6-(tert-butyl-NNO-azoxy)-5-methylthio-1,2,3,4-tetrazine 1,3-dioxide (1) was developed. This compound is likely to be a precursor of tetrazino-tetrazine 1,3,6,8-tetraoxide. The synthetic strategy consists of four steps: a synthesis of bis(tert-butyl-NNO-azoxy) methane, coupling of the latter with dimethyl nitrodi-thioimidocarbonate to give N-nitroimine 3, O-alkylation of the latter to O-alkylated nitroenamine and its reaction with BF3 center dot Et2O to afford tetrazine 1,3-dioxide 1. An X-ray diffraction study of 1 was accomplished.