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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
Author(s) -
Klenov Michael S.,
Anikin Oleg V.,
Churakov Aleksandr M.,
Strelenko Yurii A.,
Fedyanin Ivan V.,
Ananyev Ivan V.,
Tartakovsky Vladimir A.
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500923
Subject(s) - tetrazine , azoxy , chemistry , alkylation , medicinal chemistry , organic chemistry , catalysis
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 nitrodithioimidocarbonate to give N ‐nitroimine 3 , O ‐alkylation of the latter to O ‐alkylated nitroenamine and its reaction with BF 3 · Et 2 O to afford tetrazine 1,3‐dioxide 1 . An X‐ray diffraction study of 1 was accomplished.