Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates
Four new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1988/05/25, Vol.36(5), pp.1669-1675 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1675 |
|---|---|
| container_issue | 5 |
| container_start_page | 1669 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 36 |
| creator | FURUYA, SYUICHI OMURA, KIYOSHI FURUKAWA, YOSHIYASU |
| description | Four new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When 6 was treated with acid, a novel ring transformation occurred to give methyl (6-ethoxycarbonyl-3, 4-dihydro-4-oxopyrimidin-5-yl)acetates (12). |
| doi_str_mv | 10.1248/cpb.36.1669 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1460155728</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3132479191</sourcerecordid><originalsourceid>FETCH-LOGICAL-c582t-ab374e92055b35c2cf64a6707a2f6c79b588b50228007fb7eb6475e2689608b73</originalsourceid><addsrcrecordid>eNpF0LtOwzAUBmALgUQpTLxAJNhQii_xJWPFXUKCAWbLdhzqKo2L7UqEgWfHoQUWezj_-Wz9AJwiOEO4EpdmrWeEzRBj9R6YIFLxkmJM9sEEQliXmDByCI5iXEKIKeRkAr7mTeOS833h26Iqb9LCfwxu5Rr16Tsbi-SLa7eyaTF0xdzYNHS2t40zKugc7FSyheqb4iWoPrY-rNSvlRa2yPbGpB_keQij6vqSljsq78ZjcNCqLtqT3T0Fr7c3L1f35ePT3cPV_LE0VOBUKk14ZWsMKdWEGmxaVinGIVe4ZYbXmgqhKcRYQMhbza1mFacWM1EzKDQnU3C2ddfBv29sTHLpN6HPT0pUMYgo5Vjk1MU2ZYKPMdhWrvOvVRgkgnIsWOaCJWFyLDinz3emikZ1ba7AuPi3wjHGqBrR621sGZN6s39zFZIznR1JVFMxsnR7jPr_eKGCtD35Bqdok6o</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1460155728</pqid></control><display><type>article</type><title>Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates</title><source>J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>FURUYA, SYUICHI ; OMURA, KIYOSHI ; FURUKAWA, YOSHIYASU</creator><creatorcontrib>FURUYA, SYUICHI ; OMURA, KIYOSHI ; FURUKAWA, YOSHIYASU</creatorcontrib><description>Four new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When 6 was treated with acid, a novel ring transformation occurred to give methyl (6-ethoxycarbonyl-3, 4-dihydro-4-oxopyrimidin-5-yl)acetates (12).</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.36.1669</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Chemistry ; dimethyl acetylenedicarboxylate ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Organic chemistry ; Preparations and properties</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1988/05/25, Vol.36(5), pp.1669-1675</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>1989 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 1988</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c582t-ab374e92055b35c2cf64a6707a2f6c79b588b50228007fb7eb6475e2689608b73</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7222148$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>FURUYA, SYUICHI</creatorcontrib><creatorcontrib>OMURA, KIYOSHI</creatorcontrib><creatorcontrib>FURUKAWA, YOSHIYASU</creatorcontrib><title>Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Four new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When 6 was treated with acid, a novel ring transformation occurred to give methyl (6-ethoxycarbonyl-3, 4-dihydro-4-oxopyrimidin-5-yl)acetates (12).</description><subject>Chemistry</subject><subject>dimethyl acetylenedicarboxylate</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNpF0LtOwzAUBmALgUQpTLxAJNhQii_xJWPFXUKCAWbLdhzqKo2L7UqEgWfHoQUWezj_-Wz9AJwiOEO4EpdmrWeEzRBj9R6YIFLxkmJM9sEEQliXmDByCI5iXEKIKeRkAr7mTeOS833h26Iqb9LCfwxu5Rr16Tsbi-SLa7eyaTF0xdzYNHS2t40zKugc7FSyheqb4iWoPrY-rNSvlRa2yPbGpB_keQij6vqSljsq78ZjcNCqLtqT3T0Fr7c3L1f35ePT3cPV_LE0VOBUKk14ZWsMKdWEGmxaVinGIVe4ZYbXmgqhKcRYQMhbza1mFacWM1EzKDQnU3C2ddfBv29sTHLpN6HPT0pUMYgo5Vjk1MU2ZYKPMdhWrvOvVRgkgnIsWOaCJWFyLDinz3emikZ1ba7AuPi3wjHGqBrR621sGZN6s39zFZIznR1JVFMxsnR7jPr_eKGCtD35Bqdok6o</recordid><startdate>1988</startdate><enddate>1988</enddate><creator>FURUYA, SYUICHI</creator><creator>OMURA, KIYOSHI</creator><creator>FURUKAWA, YOSHIYASU</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>1988</creationdate><title>Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates</title><author>FURUYA, SYUICHI ; OMURA, KIYOSHI ; FURUKAWA, YOSHIYASU</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c582t-ab374e92055b35c2cf64a6707a2f6c79b588b50228007fb7eb6475e2689608b73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Chemistry</topic><topic>dimethyl acetylenedicarboxylate</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>FURUYA, SYUICHI</creatorcontrib><creatorcontrib>OMURA, KIYOSHI</creatorcontrib><creatorcontrib>FURUKAWA, YOSHIYASU</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>FURUYA, SYUICHI</au><au>OMURA, KIYOSHI</au><au>FURUKAWA, YOSHIYASU</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1988</date><risdate>1988</risdate><volume>36</volume><issue>5</issue><spage>1669</spage><epage>1675</epage><pages>1669-1675</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Four new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When 6 was treated with acid, a novel ring transformation occurred to give methyl (6-ethoxycarbonyl-3, 4-dihydro-4-oxopyrimidin-5-yl)acetates (12).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.36.1669</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1988/05/25, Vol.36(5), pp.1669-1675 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_journals_1460155728 |
| source | J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Chemistry dimethyl acetylenedicarboxylate Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties |
| title | Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-15T03%3A41%3A04IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Addition%20of%204-Ethoxyimidazoles%20to%20Dimethyl%20Acetylenedicarboxylate%20and%20Transformation%20of%20the%20Adducts%20to%20Pyrimidin-5-yl%20Acetates&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=FURUYA,%20SYUICHI&rft.date=1988&rft.volume=36&rft.issue=5&rft.spage=1669&rft.epage=1675&rft.pages=1669-1675&rft.issn=0009-2363&rft.eissn=1347-5223&rft.coden=CPBTAL&rft_id=info:doi/10.1248/cpb.36.1669&rft_dat=%3Cproquest_cross%3E3132479191%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1460155728&rft_id=info:pmid/&rfr_iscdi=true |