Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine
A convenient preparation method was developed for 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine by substituting one nitro group of 4,4″-dinitro-3,3′:4′,3″-ter-1,2,5-oxadiazole at treating with equivalent quantity of ammonia in solvents of low polarity. In the reaction of the obtained amino-nitro d...
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| Veröffentlicht in: | Russian journal of organic chemistry 2016, Vol.52 (8), p.1194-1202 |
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| container_title | Russian journal of organic chemistry |
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| creator | Astrat’ev, A. A. Stepanov, A. I. Sannikov, V. S. Dashko, D. V. |
| description | A convenient preparation method was developed for 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine by substituting one nitro group of 4,4″-dinitro-3,3′:4′,3″-ter-1,2,5-oxadiazole at treating with equivalent quantity of ammonia in solvents of low polarity. In the reaction of the obtained amino-nitro derivative with
N
- and
О
- nucleophiles depending on the reaction conditions and the nucleophile nature either substitution of the nitro group occurs for the nucleophile residue to form 4″-alkoxy-, azido-, hydraznyl- or mono- and dialkylamino-[3,3′;4′,3″]-ter(1,2,5-oxadiazol)-4-ylamines, or the compound suffers an intramolecular cyclization affording 7
Н
-tri-1,2,5-oxadiazolo[3,4-b:3′,4′-d:3″,4″-
f
]azepines. |
| doi_str_mv | 10.1134/S1070428016080170 |
| format | Article |
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N
- and
О
- nucleophiles depending on the reaction conditions and the nucleophile nature either substitution of the nitro group occurs for the nucleophile residue to form 4″-alkoxy-, azido-, hydraznyl- or mono- and dialkylamino-[3,3′;4′,3″]-ter(1,2,5-oxadiazol)-4-ylamines, or the compound suffers an intramolecular cyclization affording 7
Н
-tri-1,2,5-oxadiazolo[3,4-b:3′,4′-d:3″,4″-
f
]azepines.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428016080170</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Ammonia ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Nucleophiles ; Organic Chemistry ; Substitution reactions</subject><ispartof>Russian journal of organic chemistry, 2016, Vol.52 (8), p.1194-1202</ispartof><rights>Pleiades Publishing, Ltd. 2016</rights><rights>Copyright Springer Science & Business Media 2016</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c316t-f7c38618f914eb2dda9c9c51640e813d5ca3d5888134c85f9883c4e69241f8063</citedby><cites>FETCH-LOGICAL-c316t-f7c38618f914eb2dda9c9c51640e813d5ca3d5888134c85f9883c4e69241f8063</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428016080170$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428016080170$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27922,27923,41486,42555,51317</link.rule.ids></links><search><creatorcontrib>Astrat’ev, A. A.</creatorcontrib><creatorcontrib>Stepanov, A. I.</creatorcontrib><creatorcontrib>Sannikov, V. S.</creatorcontrib><creatorcontrib>Dashko, D. V.</creatorcontrib><title>Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>A convenient preparation method was developed for 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine by substituting one nitro group of 4,4″-dinitro-3,3′:4′,3″-ter-1,2,5-oxadiazole at treating with equivalent quantity of ammonia in solvents of low polarity. In the reaction of the obtained amino-nitro derivative with
N
- and
О
- nucleophiles depending on the reaction conditions and the nucleophile nature either substitution of the nitro group occurs for the nucleophile residue to form 4″-alkoxy-, azido-, hydraznyl- or mono- and dialkylamino-[3,3′;4′,3″]-ter(1,2,5-oxadiazol)-4-ylamines, or the compound suffers an intramolecular cyclization affording 7
Н
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f
]azepines.</description><subject>Ammonia</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Nucleophiles</subject><subject>Organic Chemistry</subject><subject>Substitution reactions</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp1kMFKAzEQhoMoWKsP4G3Ba6Mzm-w2602KVaHgoXpeYjaxKd1NTbZgPfWZ2jfqk5ilHgTxMvMx8___wBByiXCNyPjNFGEIPBWAOcQyhCPS65AyVrDjyHFNu_0pOQthDgAcOesRM1037UwHGxLZVElwtU7UTNdWyUUE6aVqtbehtSokziR8v9nRxrbeUTZg-832Nk62He1oFFIcpIOMuk9ZWfnlFpRTWdtGn5MTIxdBX_z0Pnkd37-MHunk-eFpdDehimHeUjNUTOQoTIFcv6VVJQtVqAxzDlogqzIlYxEiMlciM4UQTHGdFylHIyBnfXJ1yF1697HSoS3nbuWbeLJEISBm5wKiCg8q5V0IXpty6W0t_bpEKLt3ln_eGT3pwROitnnX_lfyv6ZvgiN3ow</recordid><startdate>2016</startdate><enddate>2016</enddate><creator>Astrat’ev, A. A.</creator><creator>Stepanov, A. I.</creator><creator>Sannikov, V. S.</creator><creator>Dashko, D. V.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>2016</creationdate><title>Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine</title><author>Astrat’ev, A. A. ; Stepanov, A. I. ; Sannikov, V. S. ; Dashko, D. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c316t-f7c38618f914eb2dda9c9c51640e813d5ca3d5888134c85f9883c4e69241f8063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Ammonia</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Nucleophiles</topic><topic>Organic Chemistry</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Astrat’ev, A. A.</creatorcontrib><creatorcontrib>Stepanov, A. I.</creatorcontrib><creatorcontrib>Sannikov, V. S.</creatorcontrib><creatorcontrib>Dashko, D. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Astrat’ev, A. A.</au><au>Stepanov, A. I.</au><au>Sannikov, V. S.</au><au>Dashko, D. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2016</date><risdate>2016</risdate><volume>52</volume><issue>8</issue><spage>1194</spage><epage>1202</epage><pages>1194-1202</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>A convenient preparation method was developed for 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine by substituting one nitro group of 4,4″-dinitro-3,3′:4′,3″-ter-1,2,5-oxadiazole at treating with equivalent quantity of ammonia in solvents of low polarity. In the reaction of the obtained amino-nitro derivative with
N
- and
О
- nucleophiles depending on the reaction conditions and the nucleophile nature either substitution of the nitro group occurs for the nucleophile residue to form 4″-alkoxy-, azido-, hydraznyl- or mono- and dialkylamino-[3,3′;4′,3″]-ter(1,2,5-oxadiazol)-4-ylamines, or the compound suffers an intramolecular cyclization affording 7
Н
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f
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| subjects | Ammonia Chemical synthesis Chemistry Chemistry and Materials Science Nucleophiles Organic Chemistry Substitution reactions |
| title | Synthesis and some chemical characteristics of 4″-nitro-3,3′:4′,3″-ter-1,2,5-oxadiazol-4-amine |
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