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Synthesis of 1,2,3,4‐Tetrazine 1,3‐Dioxides Annulated with 1(2)‐Aryl‐1,2,3‐triazoles
Author(s) -
Voronin Alexey A.,
Churakov Aleksandr M.,
Klenov Michael S.,
Strelenko Yurii A.,
Fedyanin Ivan V.,
Tartakovsky Vladimir A.
Publication year - 2017
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.201700750
Subject(s) - azoxy , tetrazine , chemistry , aryl , nuclear magnetic resonance spectroscopy , acetonitrile , amine gas treating , stereochemistry , medicinal chemistry , organic chemistry , alkyl
A two‐step synthetic approach to previously unknown 1,2,3,4‐tetrazine 1,3‐dioxides annulated with 1(2)‐aryl‐1,2,3‐triazoles was developed. The first step involved the formation of 5‐amine‐4‐( tert ‐butyl‐ NNO ‐azoxy)‐1(2)‐aryl‐1(2) H ‐1,2,3‐triazoles starting from ( tert ‐butyl‐ NNO ‐azoxy)acetonitrile. The second step included their cyclization to give the titled triazolotetrazines. Their structures were confirmed by 1 H NMR, 13 C NMR, and 14 N NMR spectroscopy; HRMS; and X‐ray diffraction studies. Common features and distinctions in the molecular structures of these compounds, including aromaticity, were explored.