{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T19:02:30Z","timestamp":1788289350490,"version":"build-2803163510"},"reference-count":25,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2020,4,28]],"date-time":"2020-04-28T00:00:00Z","timestamp":1588032000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>\u03b1-Nitrocinnamate underwent the conjugate addition of an active methylene compound such as nitroacetate, 1,3-dicarbonyl compound, or \u03b1-nitroketone, and the following ring closure afforded functionalized heterocyclic frameworks. The reaction of cinnamate with nitroacetate occurs via nucleophilic substitution of a nitro group by the O-attack of the nitronate, which results in isoxazoline N-oxide. This protocol was applicable to 1,3-dicarbonyl compounds to afford dihydrofuran derivatives, including those derived from direct substitution of a nitro group caused by O-attack of enolate. It was found the reactivity was lowered by an electron-withdrawing group on the carbonyl moiety. When \u03b1-nitroketone was employed as a substrate, three kinds of products were possibly formed; of these, only isoxazoline N-oxide was identified. This result indicates that the substituting ability of nitronate is higher than that of enolate for the direct SN2 substitution of a nitro group.<\/jats:p>","DOI":"10.3390\/molecules25092048","type":"journal-article","created":{"date-parts":[[2020,4,29]],"date-time":"2020-04-29T01:24:18Z","timestamp":1588123458000},"page":"2048","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Comparison of Substituting Ability of Nitronate versus Enolate for Direct Substitution of a Nitro Group"],"prefix":"10.3390","volume":"25","author":[{"given":"Yusuke","family":"Mukaijo","sequence":"first","affiliation":[{"name":"School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Soichi","family":"Yokoyama","sequence":"additional","affiliation":[{"name":"School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan"},{"name":"Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan"},{"name":"The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6052-8697","authenticated-orcid":false,"given":"Nagatoshi","family":"Nishiwaki","sequence":"additional","affiliation":[{"name":"School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan"},{"name":"Research Center for Molecular Design, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,4,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"13691","DOI":"10.1021\/acs.joc.8b01865","article-title":"Alkynylation and cyanation of alkenes using diverse properties of a nitro group","volume":"83","author":"Asahara","year":"2018","journal-title":"J. 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