{"created":"2023-05-15T12:35:20.572824+00:00","id":248,"links":{},"metadata":{"_buckets":{"deposit":"6035bc3d-9b51-4852-a63f-da187038dec7"},"_deposit":{"created_by":2,"id":"248","owners":[2],"pid":{"revision_id":0,"type":"depid","value":"248"},"status":"published"},"_oai":{"id":"oai:kutarr.kochi-tech.ac.jp:00000248","sets":["5"]},"author_link":["1023","1022","1024","1026","1020","1021","1027","1025"],"item_2_biblio_info_7":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2011","bibliographicIssueDateType":"Issued"},"bibliographicIssueNumber":"19","bibliographicPageEnd":"6754","bibliographicPageStart":"6750","bibliographicVolumeNumber":"9","bibliographic_titles":[{"bibliographic_title":"Organic & Biomolecular Chemistry"}]}]},"item_2_description_4":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"A carbamoyl-substituted nitrile oxide was generated upon treatment of easily available 2-methyl-4-nitro-3-isoxazolin-5(2H)-one with THF (not dried); the reaction proceeded efficiently even in the absence of any special reagents and reaction conditions. The nitrile oxide caused 1,3-dipolar cycloaddition with common aliphatic nitriles or electron-rich aromatic nitriles to afford 3-functionalized 1,2,4-oxadiazoles, which are expected to serve as precursors for the preparation of a variety of functional materials by the chemical transformation of the carbamoyl group. While conventional preparative methods for 1,2,4-oxadiazoles involve the cycloaddition of an electron-rich nitrile oxide with an electron-deficient nitrile or a nitrile activated by a Lewis acid, our method employs the complementary combination of an electron-rich nitrile and an electron-deficient nitrile oxide- the inverse electron-demand 1,3-cycloaddition. The DFT calculations using B3LYP 6-31G* supported the abovementioned inverse reactivity, and also suggested the presence of an accelerating effect by the carbamoyl group as a result of hydrogen bond formation with a dipolarophilic nitrile.","subitem_description_type":"Abstract"}]},"item_2_publisher_35":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"Royal Society of Chemistry"}]},"item_2_relation_13":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isVersionOf","subitem_relation_type_id":{"subitem_relation_type_id_text":"10.1039/C1OB05682D","subitem_relation_type_select":"DOI"}}]},"item_2_rights_15":{"attribute_name":"権利（URI）","attribute_value_mlt":[{"subitem_rights":"http://pubs.rsc.org/en/Content/ArticleLanding/2011/OB/c1ob05682d#!divAbstract | http://pubs.rsc.org/en/Content/ArticleLanding/2011/OB/c1ob05682d#!divAbstract"}]},"item_2_version_type_18":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_ab4af688f83e57aa","subitem_version_type":"AM"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Nishiwaki, Nagatoshi"}],"nameIdentifiers":[{"nameIdentifier":"1020","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Kobiro, Kazuya"}],"nameIdentifiers":[{"nameIdentifier":"1021","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Hirao, Shotaro"}],"nameIdentifiers":[{"nameIdentifier":"1022","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Sawayama, Jun"}],"nameIdentifiers":[{"nameIdentifier":"1023","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Saigo, Kazuhiko"}],"nameIdentifiers":[{"nameIdentifier":"1024","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ise, Yumiko"}],"nameIdentifiers":[{"nameIdentifier":"1025","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Okajima, Yoshikazu"}],"nameIdentifiers":[{"nameIdentifier":"1026","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ariga, Masahiro"}],"nameIdentifiers":[{"nameIdentifier":"1027","nameIdentifierScheme":"WEKO"}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2019-02-13"}],"displaytype":"detail","filename":"27-18.pdf","filesize":[{"value":"215.3 kB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"27-18.pdf","url":"https://kutarr.kochi-tech.ac.jp/record/248/files/27-18.pdf"},"version_id":"fb9ffc30-6914-4703-9821-a2b365fc32b4"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles"}]},"item_type_id":"2","owner":"2","path":["5"],"pubdate":{"attribute_name":"公開日","attribute_value":"2016-03-25"},"publish_date":"2016-03-25","publish_status":"0","recid":"248","relation_version_is_last":true,"title":["Inverse electron-demand 1,3-dipolar cycloaddition of nitrile oxide with common nitriles leading to 3-functionalized 1,2,4-oxadiazoles"],"weko_creator_id":"2","weko_shared_id":-1},"updated":"2023-05-15T13:40:27.067680+00:00"}