{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1361137045257958784.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1055/s-0037-1611714"}},{"identifier":{"@type":"URI","@value":"http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1611714.pdf"}}],"dc:title":[{"@value":"Synthetic Approaches to Nitro-Substituted Isoxazoles"}],"description":[{"type":"abstract","notation":[{"@value":"<jats:p>Nitro-substituted isoxazoles are of utmost interest both as versatile intermediates for targeted organic synthesis and as perspective bioactive compounds for drug development. Nevertheless, the existing approaches to them usually lack generality and strongly depend on the position of the nitro group and on the presence of other substituents in the isoxazole ring. This review provides the first systematization of all available data concerning synthetic approaches to 3-, 4-, and 5-nitroisoxazoles. There are a number of preparative approaches to 4-nitroisoxazoles based on classical heterocyclization reactions of nitro-substituted compounds and the nitration of isoxazoles. 3-Nitro- and, especially, 5-nitroisoxazoles are much less readily available. A few methods affording 3-nitroisoxazoles have been reported, often employing the heterocyclization of unsaturated compounds by treatment with sodium nitrite. The sole general preparative method for 5-nitroisoxazoles, containing a variety of functional groups, employs the heterocyclization of electrophilic alkenes by treatment with tetranitromethane activated with triethylamine.</jats:p><jats:p>1 \tIntroduction</jats:p><jats:p>2 \tSynthesis of 4-Nitroisoxazoles</jats:p><jats:p>2.1 \tNitration of Isoxazoles</jats:p><jats:p>2.2 \tCondensations of α-Nitro Ketones or Their Oximes</jats:p><jats:p>2.3 \t1,3-Dipolar Cycloaddition of Nitrile Oxides to Acetylenes and Their Synthetic Equivalents</jats:p><jats:p>2.4\tHeterocyclization of Acetylene Derivatives by Treatment with Sodium Nitrite</jats:p><jats:p>2.5 \tHeterocyclization of Nitro Derivatives of 1,3-Diketones and Their Synthetic Equivalents</jats:p><jats:p>2.6 \tMiscellaneous Methods</jats:p><jats:p>3 \tSynthesis of 3-Nitroisoxazoles</jats:p><jats:p>3.1 \tHeterocyclization of Acetylene Derivatives or 1,3-Dihalogenoalkenes by Treatment with Sodium Nitrite</jats:p><jats:p>3.2 \tHeterocyclization of Morita–Baylis–Hillman Acetates by Treatment with Sodium Nitrite</jats:p><jats:p>3.3 \t1,3-Dipolar Cycloadditions</jats:p><jats:p>4 \tSynthesis of 5-Nitroisoxazoles</jats:p><jats:p>4.1 \t1,3-Dipolar Cycloadditions</jats:p><jats:p>4.2 \tSynthesis Using Polynitro Compounds</jats:p><jats:p>5 \tConclusion</jats:p>"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1381137045257958787","@type":"Researcher","foaf:name":[{"@value":"Elena Averina"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry, Lomonosov Moscow State University"},{"@value":"IPhaC RAS"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045257958784","@type":"Researcher","foaf:name":[{"@value":"Dmitry Vasilenko"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry, Lomonosov Moscow State University"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045257958786","@type":"Researcher","foaf:name":[{"@value":"Kseniya Sedenkova"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry, Lomonosov Moscow State University"},{"@value":"IPhaC RAS"}]},{"@id":"https://cir.nii.ac.jp/crid/1381137045257958785","@type":"Researcher","foaf:name":[{"@value":"Tamara Kuznetsova"}],"jpcoar:affiliationName":[{"@value":"Department of Chemistry, Lomonosov Moscow State University"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00397881"},{"@type":"EISSN","@value":"1437210X"}],"prism:publicationName":[{"@value":"Synthesis"}],"dc:publisher":[{"@value":"Georg Thieme Verlag KG"}],"prism:publicationDate":"2019-02-27","prism:volume":"51","prism:number":"07","prism:startingPage":"1516","prism:endingPage":"1528"},"reviewed":"false","url":[{"@id":"http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1611714.pdf"}],"createdAt":"2019-02-27","modifiedAt":"2019-03-18","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1390004951536195200","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Development of Nitrolactonization Mediated by Iron(III) Nitrate Nonahydrate"}]}],"dataSourceIdentifier":[{"@type":"CROSSREF","@value":"10.1055/s-0037-1611714"},{"@type":"CROSSREF","@value":"10.1248/cpb.c20-00645_references_DOI_Rv6b8cnvpwyIHwL4sC7i4L3qw21"}]}