An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction
We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a−f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide...
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| Veröffentlicht in: | ChemInform 2003-10, Vol.68 (22), p.8583-8587 |
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| creator | Pearson, Morwenna S. M Robin, Aélig Bourgougnon, Nathalie Meslin, Jean Claude Deniaud, David |
| description | We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a−f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a−f affording β-d-uracil analogues 7a−f in good yields and with total regiocontrol. All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC). |
| doi_str_mv | 10.1021/jo034709a |
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Nucleosides and nucleotides ; Chemistry ; Disaccharides - chemistry ; Exact sciences and technology ; Furans - chemistry ; Glycosides - chemistry ; Heterocyclic Compounds - chemical synthesis ; Isothiocyanates - chemistry ; Life Sciences ; Magnetic Resonance Spectroscopy ; Models, Chemical ; Nucleosides, nucleotides and oligonucleotides ; Organic chemistry ; Preparations and properties ; Pyrans - chemistry ; Pyrimidine Nucleosides - chemical synthesis ; Uracil - chemistry</subject><ispartof>ChemInform, 2003-10, Vol.68 (22), p.8583-8587</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a444t-9c5c4b6b2692a91ecc6edc106649ec22db907217a64d4868c6c9a0a5a47887203</citedby><cites>FETCH-LOGICAL-a444t-9c5c4b6b2692a91ecc6edc106649ec22db907217a64d4868c6c9a0a5a47887203</cites><orcidid>0000-0001-7755-3357 ; 0000-0002-0846-1798</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo034709a$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo034709a$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15235522$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14575489$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://ubs.hal.science/hal-04764891$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Pearson, Morwenna S. 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All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC).</description><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Disaccharides - chemistry</subject><subject>Exact sciences and technology</subject><subject>Furans - chemistry</subject><subject>Glycosides - chemistry</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Isothiocyanates - chemistry</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Models, Chemical</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrans - chemistry</subject><subject>Pyrimidine Nucleosides - chemical synthesis</subject><subject>Uracil - chemistry</subject><issn>0022-3263</issn><issn>0931-7597</issn><issn>1520-6904</issn><issn>1522-2667</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9vEzEQxS1ERdPCgS-AfAEJoQX_9_oYhTYtCtCWIg4IWbNeL7jdrMt6FzXfvg6JkgsSc_Fo_NObN3oIPafkLSWMvruJhAtNDDxCEyoZKZQh4jGaEMJYwZnih-gopRuSS0r5BB1SIbUUpZmgb9MOnzRNcMF3A76K4-DxEPHFqg_LUIfO40-ja31MofZ42kEbf44-4WqFvwv8BrMfeLZybYS6DkOIHb7y4NbNU3TQQJv8s-17jL6enlzPzorF5_n5bLooQAgxFMZJJypVMWUYGOqdU752lCgljHeM1ZUhmlENStSiVKVTzgABCUKXpWaEH6PXG91f0Nq7bBr6lY0Q7Nl0YdczIrTKl9I_NLOvNuxdH3_nKwa7DMn5toXOxzFZTTkRkrP_glRrzg1j--2ujyn1vtlZoMSuo7G7aDL7Yis6Vktf78ltFhl4uQUgOWibHjoX0p6TjEv5d2mx4UIa_P3uH_pbqzTX0l5ffLEf9eX8vZ5_sJd7XXAp-xn7nGL6h8EHzOuuAw</recordid><startdate>20031031</startdate><enddate>20031031</enddate><creator>Pearson, Morwenna S. 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M</creatorcontrib><creatorcontrib>Robin, Aélig</creatorcontrib><creatorcontrib>Bourgougnon, Nathalie</creatorcontrib><creatorcontrib>Meslin, Jean Claude</creatorcontrib><creatorcontrib>Deniaud, David</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>ChemInform</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pearson, Morwenna S. M</au><au>Robin, Aélig</au><au>Bourgougnon, Nathalie</au><au>Meslin, Jean Claude</au><au>Deniaud, David</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction</atitle><jtitle>ChemInform</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-10-31</date><risdate>2003</risdate><volume>68</volume><issue>22</issue><spage>8583</spage><epage>8587</epage><pages>8583-8587</pages><issn>0022-3263</issn><issn>0931-7597</issn><eissn>1520-6904</eissn><eissn>1522-2667</eissn><coden>JOCEAH</coden><abstract>We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a−f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a−f affording β-d-uracil analogues 7a−f in good yields and with total regiocontrol. All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14575489</pmid><doi>10.1021/jo034709a</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-7755-3357</orcidid><orcidid>https://orcid.org/0000-0002-0846-1798</orcidid></addata></record> |
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| subjects | Carbohydrates. Nucleosides and nucleotides Chemistry Disaccharides - chemistry Exact sciences and technology Furans - chemistry Glycosides - chemistry Heterocyclic Compounds - chemical synthesis Isothiocyanates - chemistry Life Sciences Magnetic Resonance Spectroscopy Models, Chemical Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties Pyrans - chemistry Pyrimidine Nucleosides - chemical synthesis Uracil - chemistry |
| title | An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction |
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