{"@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/1390282679366237184.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1246/nikkashi.1985.725"}},{"identifier":{"@type":"URI","@value":"https://www.jstage.jst.go.jp/article/nikkashi1972/1985/4/1985_4_725/_pdf"}},{"identifier":{"@type":"NAID","@value":"130004158109"}}],"dc:title":[{"@language":"en","@value":"Synthesis of Dihydronaphthothiopyrans by the Acid-catalyzed Reaction of 2-Naphthalenethiol with Acrylaldehyde"},{"@language":"ja","@value":"2-ナフタレンチオールとアクリルアルデヒドとの反応によるジヒドロナフトチオピラン類の合成"}],"description":[{"type":"abstract","notation":[{"@language":"en","@value":"Naphthothiopyrans were synthesized easily by the addition reaction of 2-naphthalenethiol (NT) with acrylaldehyde(AA) followed by the ringclosure reaction in the presence of acid catalysts in dry ether.<BR>The yields of naphthothiopyrans such as 1-(2-naphthylthio)-2, 3-dihydro-1 H-naphtho[2, 1-b]thiopyran [2 a], 2, 3-dihydro-1 H-naphtho[2, 1-b]thiopyran [3], 3 H-naphtho[2, 1-b]thiopyran [4] and 3 H-naphtho[2, 1-b]thiopyran-3-one [5] were varied according to the reaction conditions. For instance, the reaction of NT(1.0 mol) with AA (0.5 mol) in the presence of 1.0 mol of sulfuric acid gave [2 a] in a 96% yield. Another reaction of equimolar amounts of NT and AA with 1.0 mol of sulfuric acid yielded the naphthothiopyrans [2a], [3], [4]. and [5] in 43%, 18%, 7% and 7% yields, respectively.<BR>However, a decrease of the amount of sulfuric acid to 0.1 mol afforded the intermediate, 3-(2-naphthylthio) propionaldehyde [1] in 95% yield. Whereas the similar treatment of NT (1.0 mol) with AA(0.5 mol) yielded [2a] in 96%.<BR>In cyclization of some thiols with [1], th e corresponding dihydronaphthothiopyran sulfides have been produced.<BR>On the basis o f these results, possible reaction paths have been discussed."},{"@language":"ja","@value":"2-ナフタレンチオール(NT)とアクリルアルデヒド(AA)をエーテル中硫酸触媒の存在下で反応させると,付加反臨についで閉環反応が容易に起こり,1-(2-ナフチルチオ)-2,3-ジヒドロ-1H-ナフト[2,1-b]チオピラン[2a],2,3-ジヒドロ-1H-ナフト[2,1-b]チオピラン[3],3H-ナフト[2,1-b]チオピラン[4]および 3H-ナフト[2,1-b]チオピラン-3-オン[5]などのナフトチオピラン類を生成した。<BR>生成物の収率は反応条件によって大きく変化した。<BR>すなわち NT1 mo lと AA O.5mol を 1mo1の硫酸存在下で反応させると, 96% の収率で[2a]が生成したが,同モルの NT と AA との反応では[2a]43,[3]18,[4]7,[5]7%をそれぞれ生成した。しかし同モルの NT と AA との反応で硫酸量を 0.1mol に減少させると,反応中間体である 3-(2-ナフチルチオ)プロピオンアルデヒドが 95% 得られた。また NTlmol と AA O.5mol の反応では硫酸量(0.1または1mol)に[1]関係なく,[2a]を 96% 生成した。さらに[1]とチオール類との反応によっても対応するジヒドロナフトチオピランのスルフィド類が生成した。<BR>以上の反応経路についても検討を加えた。"}],"abstractLicenseFlag":"disallow"}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1410851320456816257","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000256044495"}],"foaf:name":[{"@language":"en","@value":"NAKAZAWA Toshikatsu"},{"@language":"ja","@value":"中沢 利勝"}],"jpcoar:affiliationName":[{"@language":"ja","@value":"日本大学理工学部工業化学科"},{"@language":"en","@value":"Department of Industrial Chemistry College of Science and Technology, Nihon University;"}]},{"@id":"https://cir.nii.ac.jp/crid/1410851320456816258","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000256044496"}],"foaf:name":[{"@language":"en","@value":"TAKAGAKI Nobuaki"},{"@language":"ja","@value":"高垣 信明"}],"jpcoar:affiliationName":[{"@language":"ja","@value":"日本大学理工学部工業化学科"},{"@language":"en","@value":"Department of Industrial Chemistry College of Science and Technology, Nihon University;"}]},{"@id":"https://cir.nii.ac.jp/crid/1420282801182602880","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"10272709"},{"@type":"NRID","@value":"1000010272709"},{"@type":"NRID","@value":"9000258716427"},{"@type":"NRID","@value":"9000257710968"},{"@type":"NRID","@value":"9000257726072"},{"@type":"NRID","@value":"9000257727184"},{"@type":"NRID","@value":"9000001679386"},{"@type":"NRID","@value":"9000000618215"},{"@type":"NRID","@value":"9000255838017"},{"@type":"NRID","@value":"9000025051184"},{"@type":"NRID","@value":"9000256019652"},{"@type":"NRID","@value":"9000256028507"},{"@type":"NRID","@value":"9000257725845"},{"@type":"NRID","@value":"9000024364380"},{"@type":"NRID","@value":"9000021386305"},{"@type":"NRID","@value":"9000002977214"},{"@type":"NRID","@value":"9000001151291"},{"@type":"NRID","@value":"9000283869308"},{"@type":"NRID","@value":"9000356514109"},{"@type":"NRID","@value":"9000240082966"},{"@type":"NRID","@value":"9000255699714"},{"@type":"NRID","@value":"9000257715581"},{"@type":"NRID","@value":"9000009154818"},{"@type":"NRID","@value":"9000242715279"},{"@type":"NRID","@value":"9000008761733"},{"@type":"NRID","@value":"9000021037047"},{"@type":"NRID","@value":"9000017527984"},{"@type":"NRID","@value":"9000283870018"},{"@type":"NRID","@value":"9000256355905"},{"@type":"NRID","@value":"9000000420299"},{"@type":"NRID","@value":"9000258392995"},{"@type":"NRID","@value":"9000257722394"},{"@type":"NRID","@value":"9000335191931"},{"@type":"NRID","@value":"9000258393782"},{"@type":"NRID","@value":"9000256026828"},{"@type":"NRID","@value":"9000257728643"},{"@type":"NRID","@value":"9000256044497"},{"@type":"NRID","@value":"9000020964497"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0047199"}],"foaf:name":[{"@language":"en","@value":"SHIMIZU Masaki"},{"@language":"ja","@value":"清水 正樹"}],"jpcoar:affiliationName":[{"@language":"ja","@value":"日本大学理工学部工業化学科"},{"@language":"en","@value":"Department of Industrial Chemistry College of Science and Technology, Nihon University;"}]},{"@id":"https://cir.nii.ac.jp/crid/1410006850497139841","@type":"Researcher","personIdentifier":[{"@type":"NRID","@value":"9000255708782"}],"foaf:name":[{"@language":"en","@value":"ITABASHI Kunio"},{"@language":"ja","@value":"板橋 国夫"}],"jpcoar:affiliationName":[{"@language":"ja","@value":"日本大学理工学部工業化学科"},{"@language":"en","@value":"Department of Industrial Chemistry College of Science and Technology, Nihon University;"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"03694577"},{"@type":"EISSN","@value":"21850925"}],"prism:publicationName":[{"@language":"en","@value":"NIPPON KAGAKU KAISHI"},{"@language":"ja","@value":"日本化学会誌（化学と工業化学）"},{"@language":"en","@value":"Nippon Kagaku Kaishi"},{"@language":"ja","@value":"日化"},{"@language":"en","@value":"NIPPON KAGAKU KAISHI"},{"@language":"ja","@value":"日本化学会誌"}],"dc:publisher":[{"@language":"en","@value":"The Chemical Society of Japan"},{"@language":"ja","@value":"公益社団法人 日本化学会"}],"prism:publicationDate":"1985-04-10","prism:volume":"1985","prism:number":"4","prism:startingPage":"725","prism:endingPage":"730"},"reviewed":"false","url":[{"@id":"https://www.jstage.jst.go.jp/article/nikkashi1972/1985/4/1985_4_725/_pdf"}],"availableAt":"1985-04-10","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=General%20Chemistry","dc:title":"General Chemistry"}],"dataSourceIdentifier":[{"@type":"JALC","@value":"oai:japanlinkcenter.org:0020537127"},{"@type":"CROSSREF","@value":"10.1246/nikkashi.1985.725"},{"@type":"CIA","@value":"130004158109"}]}