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Oxygen‐Rich 1,2,4‐Triazolo[3,4‐ d ]‐1,2,4‐triazolo[3,4‐ f ]furazano[3,4‐ b ]pyrazines as Energetic Materials
Author(s) -
Sheremetev Aleksei B.,
Korolev Vecheslav L.,
Potemkin Aleksandr A.,
Aleksandrova Natali S.,
Palysaeva Nadezhda V.,
Hoang Trung H.,
Sinditskii Valery P.,
Suponitsky Kyrill Yu.
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600386
Subject(s) - chemistry , pyrazine , propellant , oxygen , explosive material , energetic material , reaction conditions , oxygen atom , medicinal chemistry , organic chemistry , molecule , catalysis
A convenient one‐pot synthesis of 5,10‐bis(trinitromethyl)‐ ( 5 ) and 5,10‐bis(fluorodinitromethyl)furazano[3,4‐ e ]di([1,2,4]triazolo)[4,3‐ a :3′,4′‐ c ]pyrazines ( 6 ) by employing the reaction of 5,6‐dichlorofurazano[3,4‐ b ]pyrazine with 5‐(trinitromethyl)‐ and 5‐(1‐fluoro‐1,1‐dinitromethyl)tetrazoles, respectively, was developed. The protocol was carried out under mild conditions at a moderate temperature and over short reaction times to synthesize the products in excellent yields. For the first time, these polynitromethyl‐substituted compounds, which may have potential use as explosive and propellant materials, have been fully characterized. The burning rate of compound 5 was shown to be slightly superior to that of 2,4,6,8,10,12‐hexanitrohexaazaisowurtzitane (CL‐20).