Addition Reactions of Heterocumulenes. IV. Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines

Addition Reactions of Heterocumulenes. IV. Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines

The reactions of diketene with S, S-dimethyl-N-2-pyridinylsulfilimine (IVa) and N-2-benzothiazolyl-S, S-dimethylsulfilimine (IVb) gave 2-(2-dimethylsulfuranylideneaceto-acetamido) pyridine (VIa) and 2-(2-dimethylsulfuranylideneacetoacetamido) benzothiazole (VIb), respectively. However, the reaction...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1979/09/25, Vol.27(9), pp.2116-2121
Hauptverfasser: SAKAMOTO, MASANORI, MIYAZAWA, KYOKO, KUWABARA, KEIKO, TOMIMATSU, YOSHIO
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container_end_page 2121
container_issue 9
container_start_page 2116
container_title Chemical & pharmaceutical bulletin
container_volume 27
creator SAKAMOTO, MASANORI
MIYAZAWA, KYOKO
KUWABARA, KEIKO
TOMIMATSU, YOSHIO
description The reactions of diketene with S, S-dimethyl-N-2-pyridinylsulfilimine (IVa) and N-2-benzothiazolyl-S, S-dimethylsulfilimine (IVb) gave 2-(2-dimethylsulfuranylideneaceto-acetamido) pyridine (VIa) and 2-(2-dimethylsulfuranylideneacetoacetamido) benzothiazole (VIb), respectively. However, the reaction of diketene with S, S-dimethyl-N-(4-nitrophenyl) sulfilimine (IVc) and N-2-benzoxazolyl-S, S-dimethylsulfilimine (IVd) gave 3-acetyl-4-hydroxy-6-methyl-1-(4-nitrophenyl)-2-pyridone (VIIc) and 3-acetyl-1-(2-benzoxazolyl)-4-hydroxy-6-methyl-2-pyridone (VIId), respectively. On the other hand, the reaction of diphenylketene with sulfilimines (IVa, IVb, and IVd) gave the corresponding 1, 3-cyclization products (VIII, IX, and X).
doi_str_mv 10.1248/cpb.27.2116
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IV. Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines</title><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>J-STAGE (Japan Science &amp; Technology Information Aggregator, Electronic) Freely Available Titles - Japanese</source><source>Free Full-Text Journals in Chemistry</source><creator>SAKAMOTO, MASANORI ; MIYAZAWA, KYOKO ; KUWABARA, KEIKO ; TOMIMATSU, YOSHIO</creator><creatorcontrib>SAKAMOTO, MASANORI ; MIYAZAWA, KYOKO ; KUWABARA, KEIKO ; TOMIMATSU, YOSHIO</creatorcontrib><description>The reactions of diketene with S, S-dimethyl-N-2-pyridinylsulfilimine (IVa) and N-2-benzothiazolyl-S, S-dimethylsulfilimine (IVb) gave 2-(2-dimethylsulfuranylideneaceto-acetamido) pyridine (VIa) and 2-(2-dimethylsulfuranylideneacetoacetamido) benzothiazole (VIb), respectively. However, the reaction of diketene with S, S-dimethyl-N-(4-nitrophenyl) sulfilimine (IVc) and N-2-benzoxazolyl-S, S-dimethylsulfilimine (IVd) gave 3-acetyl-4-hydroxy-6-methyl-1-(4-nitrophenyl)-2-pyridone (VIIc) and 3-acetyl-1-(2-benzoxazolyl)-4-hydroxy-6-methyl-2-pyridone (VIId), respectively. On the other hand, the reaction of diphenylketene with sulfilimines (IVa, IVb, and IVd) gave the corresponding 1, 3-cyclization products (VIII, IX, and X).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.27.2116</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>addition</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1979/09/25, Vol.27(9), pp.2116-2121</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1979</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3386-8b4f576d20cf461f09c4603aec364eae1fd5801421299304bed612f6ee1973053</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,1884,4025,27928,27929,27930</link.rule.ids></links><search><creatorcontrib>SAKAMOTO, MASANORI</creatorcontrib><creatorcontrib>MIYAZAWA, KYOKO</creatorcontrib><creatorcontrib>KUWABARA, KEIKO</creatorcontrib><creatorcontrib>TOMIMATSU, YOSHIO</creatorcontrib><title>Addition Reactions of Heterocumulenes. IV. Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines</title><title>Chemical &amp; pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>The reactions of diketene with S, S-dimethyl-N-2-pyridinylsulfilimine (IVa) and N-2-benzothiazolyl-S, S-dimethylsulfilimine (IVb) gave 2-(2-dimethylsulfuranylideneaceto-acetamido) pyridine (VIa) and 2-(2-dimethylsulfuranylideneacetoacetamido) benzothiazole (VIb), respectively. However, the reaction of diketene with S, S-dimethyl-N-(4-nitrophenyl) sulfilimine (IVc) and N-2-benzoxazolyl-S, S-dimethylsulfilimine (IVd) gave 3-acetyl-4-hydroxy-6-methyl-1-(4-nitrophenyl)-2-pyridone (VIIc) and 3-acetyl-1-(2-benzoxazolyl)-4-hydroxy-6-methyl-2-pyridone (VIId), respectively. 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Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines</title><author>SAKAMOTO, MASANORI ; MIYAZAWA, KYOKO ; KUWABARA, KEIKO ; TOMIMATSU, YOSHIO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3386-8b4f576d20cf461f09c4603aec364eae1fd5801421299304bed612f6ee1973053</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1979</creationdate><topic>addition</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SAKAMOTO, MASANORI</creatorcontrib><creatorcontrib>MIYAZAWA, KYOKO</creatorcontrib><creatorcontrib>KUWABARA, KEIKO</creatorcontrib><creatorcontrib>TOMIMATSU, YOSHIO</creatorcontrib><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical &amp; pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SAKAMOTO, MASANORI</au><au>MIYAZAWA, KYOKO</au><au>KUWABARA, KEIKO</au><au>TOMIMATSU, YOSHIO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Addition Reactions of Heterocumulenes. IV. Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines</atitle><jtitle>Chemical &amp; pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1979</date><risdate>1979</risdate><volume>27</volume><issue>9</issue><spage>2116</spage><epage>2121</epage><pages>2116-2121</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>The reactions of diketene with S, S-dimethyl-N-2-pyridinylsulfilimine (IVa) and N-2-benzothiazolyl-S, S-dimethylsulfilimine (IVb) gave 2-(2-dimethylsulfuranylideneaceto-acetamido) pyridine (VIa) and 2-(2-dimethylsulfuranylideneacetoacetamido) benzothiazole (VIb), respectively. However, the reaction of diketene with S, S-dimethyl-N-(4-nitrophenyl) sulfilimine (IVc) and N-2-benzoxazolyl-S, S-dimethylsulfilimine (IVd) gave 3-acetyl-4-hydroxy-6-methyl-1-(4-nitrophenyl)-2-pyridone (VIIc) and 3-acetyl-1-(2-benzoxazolyl)-4-hydroxy-6-methyl-2-pyridone (VIId), respectively. On the other hand, the reaction of diphenylketene with sulfilimines (IVa, IVb, and IVd) gave the corresponding 1, 3-cyclization products (VIII, IX, and X).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.27.2116</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record>
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title Addition Reactions of Heterocumulenes. IV. Reactions of Diketene and Diphenylketene with N-Aryl-S, S-dimethylsulfilimines
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