Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3, 5-Dihydroxy-7, 8-dimethoxyflavones from 3-Hydroxy-5, 7, 8-trimethoxyflavones
2-Hydroxy-3, 4, 6-trimethoxy-ω- (ρ-methoxybenzoyloxy) acetophenone was prepared from 2, 3, 4, 6-tetramethoxyacetophenone via the corresponding ω-bromoacetophenone. Cyclization of the acetophenone with ρ-methoxybenzoic anhydride by application of the Allan-Robinson reaction afforded 3-hydroxy-4'...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1987/11/25, Vol.35(11), pp.4465-4472 |
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| creator | HORIE, TOKUNARU TSUKAYAMA, MASAO KAWAMURA, YASUHIKO YAMAMOTO, SHIGEO |
| description | 2-Hydroxy-3, 4, 6-trimethoxy-ω- (ρ-methoxybenzoyloxy) acetophenone was prepared from 2, 3, 4, 6-tetramethoxyacetophenone via the corresponding ω-bromoacetophenone. Cyclization of the acetophenone with ρ-methoxybenzoic anhydride by application of the Allan-Robinson reaction afforded 3-hydroxy-4', 5, 7, 8-tetramethoxyflavone along with 2- (α-hydroxy-4-methoxybenzylidene) -4, 6, 7-trimethoxycoumaranone. The 5-methoxy group in the tosylate or mesylate of the 3-hydroxyflavone was selectively cleaved with anhydrous aluminum bromide in acetonitrile to give the corresponding 5-hydroxyflavone, which was converted into 3, 5-dihydroxy-4', 7, 8-trimethoxyflavone with anhydrous potassium carbonate in methanol. 3, 3', 4', 5-Tetrahydroxy-7, 8-dimethoxyflavone was also synthesized by a similar method. The demethylation of the 5-methoxy group in flavones with a 3-hydroxy group is applicable to the synthesis of 3, 5-dihydroxyflavones. |
| doi_str_mv | 10.1248/cpb.35.4465 |
| format | Article |
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IX. A New Method for Synthesizing 3, 5-Dihydroxy-7, 8-dimethoxyflavones from 3-Hydroxy-5, 7, 8-trimethoxyflavones</title><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese</source><source>Free Full-Text Journals in Chemistry</source><creator>HORIE, TOKUNARU ; TSUKAYAMA, MASAO ; KAWAMURA, YASUHIKO ; YAMAMOTO, SHIGEO</creator><creatorcontrib>HORIE, TOKUNARU ; TSUKAYAMA, MASAO ; KAWAMURA, YASUHIKO ; YAMAMOTO, SHIGEO</creatorcontrib><description>2-Hydroxy-3, 4, 6-trimethoxy-ω- (ρ-methoxybenzoyloxy) acetophenone was prepared from 2, 3, 4, 6-tetramethoxyacetophenone via the corresponding ω-bromoacetophenone. Cyclization of the acetophenone with ρ-methoxybenzoic anhydride by application of the Allan-Robinson reaction afforded 3-hydroxy-4', 5, 7, 8-tetramethoxyflavone along with 2- (α-hydroxy-4-methoxybenzylidene) -4, 6, 7-trimethoxycoumaranone. The 5-methoxy group in the tosylate or mesylate of the 3-hydroxyflavone was selectively cleaved with anhydrous aluminum bromide in acetonitrile to give the corresponding 5-hydroxyflavone, which was converted into 3, 5-dihydroxy-4', 7, 8-trimethoxyflavone with anhydrous potassium carbonate in methanol. 3, 3', 4', 5-Tetrahydroxy-7, 8-dimethoxyflavone was also synthesized by a similar method. The demethylation of the 5-methoxy group in flavones with a 3-hydroxy group is applicable to the synthesis of 3, 5-dihydroxyflavones.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.35.4465</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>3, 5-dihydroxy-7, 8-dimethoxyflavone ; 3-hydroxy-5, 7, 8-trimethoxyflavone ; 3-sulfonyloxy-5, 7, 8-trimethoxyflavone ; Allan-Robinson reaction ; aurone ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; selective demethylation ; tambulin ; ω-aroyloxyacetophenone</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1987/11/25, Vol.35(11), pp.4465-4472</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1988 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1987</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5015-aaefa43b52bc85b5bd2cace63b4bbaf921f2e7bed81e4885cb289594e5dcd3f53</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7499342$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>HORIE, TOKUNARU</creatorcontrib><creatorcontrib>TSUKAYAMA, MASAO</creatorcontrib><creatorcontrib>KAWAMURA, YASUHIKO</creatorcontrib><creatorcontrib>YAMAMOTO, SHIGEO</creatorcontrib><title>Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3, 5-Dihydroxy-7, 8-dimethoxyflavones from 3-Hydroxy-5, 7, 8-trimethoxyflavones</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>2-Hydroxy-3, 4, 6-trimethoxy-ω- (ρ-methoxybenzoyloxy) acetophenone was prepared from 2, 3, 4, 6-tetramethoxyacetophenone via the corresponding ω-bromoacetophenone. Cyclization of the acetophenone with ρ-methoxybenzoic anhydride by application of the Allan-Robinson reaction afforded 3-hydroxy-4', 5, 7, 8-tetramethoxyflavone along with 2- (α-hydroxy-4-methoxybenzylidene) -4, 6, 7-trimethoxycoumaranone. The 5-methoxy group in the tosylate or mesylate of the 3-hydroxyflavone was selectively cleaved with anhydrous aluminum bromide in acetonitrile to give the corresponding 5-hydroxyflavone, which was converted into 3, 5-dihydroxy-4', 7, 8-trimethoxyflavone with anhydrous potassium carbonate in methanol. 3, 3', 4', 5-Tetrahydroxy-7, 8-dimethoxyflavone was also synthesized by a similar method. The demethylation of the 5-methoxy group in flavones with a 3-hydroxy group is applicable to the synthesis of 3, 5-dihydroxyflavones.</description><subject>3, 5-dihydroxy-7, 8-dimethoxyflavone</subject><subject>3-hydroxy-5, 7, 8-trimethoxyflavone</subject><subject>3-sulfonyloxy-5, 7, 8-trimethoxyflavone</subject><subject>Allan-Robinson reaction</subject><subject>aurone</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>selective demethylation</subject><subject>tambulin</subject><subject>ω-aroyloxyacetophenone</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNpdkctuEzEUhkcIJEJhxQtYgh3x4OtkZhm1hFYqdBGQ2I18OW4cpuNgT0qHF-vr1dNErcTGlnw-f-fo_EXxnpKSMlF_NjtdclkKUckXxYxyscCSMf6ymBFCGsx4xV8Xb1LaEsIkWfBZcb8e9tZDQsGhYQNoDR2Ywd8CusLL7vfYqcGHHqneojNQzw8ZX3XqNvTB21Sii18lWqLv8Bd9g2ETLHIhovXYZ2Xy_3x_jfgcSXzmN6ON4W7EizmqsfU3E303ukdVnsLFcIM4Pj9Sco4ewSH-T74tXjnVJXh3vE-Kn6svP07P8eXV14vT5SU2klCJlQKnBNeSaVNLLbVlRhmouBZaK9cw6hgsNNiagqhraTSrG9kIkNZY7iQ_KT4cvLsY_uwhDe027GOfW7ZUVITyKi82U58OlIkhpQiu3eWJVRxbStopmTYn03LZTslk-uPRqZJRnYuqNz49fVmIpuGCZWx1wLZpUNfwVFdx8KaDSUkbWU9aSo_n5H8GNiq20PMHGNWoPA</recordid><startdate>1987</startdate><enddate>1987</enddate><creator>HORIE, TOKUNARU</creator><creator>TSUKAYAMA, MASAO</creator><creator>KAWAMURA, YASUHIKO</creator><creator>YAMAMOTO, SHIGEO</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1987</creationdate><title>Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3, 5-Dihydroxy-7, 8-dimethoxyflavones from 3-Hydroxy-5, 7, 8-trimethoxyflavones</title><author>HORIE, TOKUNARU ; TSUKAYAMA, MASAO ; KAWAMURA, YASUHIKO ; YAMAMOTO, SHIGEO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5015-aaefa43b52bc85b5bd2cace63b4bbaf921f2e7bed81e4885cb289594e5dcd3f53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>3, 5-dihydroxy-7, 8-dimethoxyflavone</topic><topic>3-hydroxy-5, 7, 8-trimethoxyflavone</topic><topic>3-sulfonyloxy-5, 7, 8-trimethoxyflavone</topic><topic>Allan-Robinson reaction</topic><topic>aurone</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>selective demethylation</topic><topic>tambulin</topic><topic>ω-aroyloxyacetophenone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>HORIE, TOKUNARU</creatorcontrib><creatorcontrib>TSUKAYAMA, MASAO</creatorcontrib><creatorcontrib>KAWAMURA, YASUHIKO</creatorcontrib><creatorcontrib>YAMAMOTO, SHIGEO</creatorcontrib><collection>Pascal-Francis</collection><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 & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>HORIE, TOKUNARU</au><au>TSUKAYAMA, MASAO</au><au>KAWAMURA, YASUHIKO</au><au>YAMAMOTO, SHIGEO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3, 5-Dihydroxy-7, 8-dimethoxyflavones from 3-Hydroxy-5, 7, 8-trimethoxyflavones</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1987</date><risdate>1987</risdate><volume>35</volume><issue>11</issue><spage>4465</spage><epage>4472</epage><pages>4465-4472</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>2-Hydroxy-3, 4, 6-trimethoxy-ω- (ρ-methoxybenzoyloxy) acetophenone was prepared from 2, 3, 4, 6-tetramethoxyacetophenone via the corresponding ω-bromoacetophenone. Cyclization of the acetophenone with ρ-methoxybenzoic anhydride by application of the Allan-Robinson reaction afforded 3-hydroxy-4', 5, 7, 8-tetramethoxyflavone along with 2- (α-hydroxy-4-methoxybenzylidene) -4, 6, 7-trimethoxycoumaranone. The 5-methoxy group in the tosylate or mesylate of the 3-hydroxyflavone was selectively cleaved with anhydrous aluminum bromide in acetonitrile to give the corresponding 5-hydroxyflavone, which was converted into 3, 5-dihydroxy-4', 7, 8-trimethoxyflavone with anhydrous potassium carbonate in methanol. 3, 3', 4', 5-Tetrahydroxy-7, 8-dimethoxyflavone was also synthesized by a similar method. The demethylation of the 5-methoxy group in flavones with a 3-hydroxy group is applicable to the synthesis of 3, 5-dihydroxyflavones.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.35.4465</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1987/11/25, Vol.35(11), pp.4465-4472 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | 3, 5-dihydroxy-7, 8-dimethoxyflavone 3-hydroxy-5, 7, 8-trimethoxyflavone 3-sulfonyloxy-5, 7, 8-trimethoxyflavone Allan-Robinson reaction aurone Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties selective demethylation tambulin ω-aroyloxyacetophenone |
| title | Studies of the Selective O-Alkylation and Dealkylation of Flavonoids. IX. A New Method for Synthesizing 3, 5-Dihydroxy-7, 8-dimethoxyflavones from 3-Hydroxy-5, 7, 8-trimethoxyflavones |
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