{"title":"Integration of 1,2,3-Triazine N-Oxide and 2,4,6-Trinitroaniline Moieties for the Design of Heat-Resistant Energetic Compounds","authors":"Wen-Hao Cui, Hao-Ran Xu, Zhiwen Ye, Ying He","doi":"10.1021/acs.orglett.5c00305","DOIUrl":null,"url":null,"abstract":"Heat-resistant energetic compounds are of great importance in the field of energetic material chemistry. Here, we report a practical synthesis of a series of fused-ring energetic compounds via the combination of 1,2,3-triazine <i>N</i>-oxide and 2,4,6-trinitroaniline moieties. Starting from the known compound 4,6-diamino-2-chloropyrimidine-5-carbonitrile (<b>1</b>), the nucleophilic substitution followed by one-step nitration introduced three nitro groups onto the benzene ring and 1,2,3-triazine <i>N</i>-oxide moiety, simultaneously. The resulting compounds <b>4</b>–<b>7</b> exhibited a high decomposition temperature (<i>T</i><sub>d</sub> > 250 °C) as well as relatively good detonation properties and low sensitivities.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"47 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00305","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Heat-resistant energetic compounds are of great importance in the field of energetic material chemistry. Here, we report a practical synthesis of a series of fused-ring energetic compounds via the combination of 1,2,3-triazine N-oxide and 2,4,6-trinitroaniline moieties. Starting from the known compound 4,6-diamino-2-chloropyrimidine-5-carbonitrile (1), the nucleophilic substitution followed by one-step nitration introduced three nitro groups onto the benzene ring and 1,2,3-triazine N-oxide moiety, simultaneously. The resulting compounds 4–7 exhibited a high decomposition temperature (Td > 250 °C) as well as relatively good detonation properties and low sensitivities.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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