An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues
An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole...
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| Veröffentlicht in: | Journal of organic chemistry 2011-02, Vol.76 (3), p.846-856 |
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| container_end_page | 856 |
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| container_issue | 3 |
| container_start_page | 846 |
| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Modha, Sachin G Trivedi, Jalpa C Mehta, Vaibhav P Ermolat’ev, Denis S Van der Eycken, Erik V |
| description | An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole linkage. The beneficial effect of microwave irradiation throughout the sequence has been demonstrated. |
| doi_str_mv | 10.1021/jo102089h |
| format | Article |
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Org. Chem</addtitle><description>An improved and convenient methodology for the synthesis of asymmetrically substituted pyrazines starting from 3,5-dichloropyrazin-2(1H)-ones has been elaborated. Several nucleoside analogues have been synthesized containing the pyrazine core as the organic base coupled with the sugar via a triazole linkage. The beneficial effect of microwave irradiation throughout the sequence has been demonstrated.</description><subject>Base Sequence</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</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>Magnetic Resonance Spectroscopy</subject><subject>Microwaves</subject><subject>Molecular Structure</subject><subject>Nucleosides - chemical synthesis</subject><subject>Nucleosides - chemistry</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrazines - chemical synthesis</subject><subject>Pyrazines - chemistry</subject><subject>Triazoles - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1LAzEQhoMotlYP_gHZi4iH1Xxuk2Op9QOKiuh5md3N1pRtUpNdtP56I63txWFgLg_vOzwInRJ8RTAl13MXD5bqfQ_1iaA4zRTm-6iPMaUpoxnroaMQ5jiOEOIQ9SihhFNG--hmZJPJ11JXpjWuC8mL61qdtO4TfJU8rzx8G6vTsbMtGGvsLHnsyka7YCqdjCw0btbpcIwOamiCPtncAXq7nbyO79Pp093DeDRNgXHeppRpPAQhQGZkqMpCSk0rWnCFIRPASqUzWgjMGaVVzRlINlQ10XFVUQFhbIAu1rlL7z5ib5svTCh104DV8flccplJyWPCAF2uydK7ELyu86U3C_CrnOD811m-dRbZs01qVyx0tSX_JEXgfANAKKGpPdjShB3HFOeMqB0HZYj5nY9-wj-FP8Opfuc</recordid><startdate>20110204</startdate><enddate>20110204</enddate><creator>Modha, Sachin G</creator><creator>Trivedi, Jalpa C</creator><creator>Mehta, Vaibhav P</creator><creator>Ermolat’ev, Denis S</creator><creator>Van der Eycken, Erik V</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20110204</creationdate><title>An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues</title><author>Modha, Sachin G ; Trivedi, Jalpa C ; Mehta, Vaibhav P ; Ermolat’ev, Denis S ; Van der Eycken, Erik V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a344t-23e07a55a86179cb88e2d2b490a65a3c9e62b504322df43a8379f1ef1e9bda133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Base Sequence</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</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>Magnetic Resonance Spectroscopy</topic><topic>Microwaves</topic><topic>Molecular Structure</topic><topic>Nucleosides - chemical synthesis</topic><topic>Nucleosides - chemistry</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyrazines - chemical synthesis</topic><topic>Pyrazines - chemistry</topic><topic>Triazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Modha, Sachin G</creatorcontrib><creatorcontrib>Trivedi, Jalpa C</creatorcontrib><creatorcontrib>Mehta, Vaibhav P</creatorcontrib><creatorcontrib>Ermolat’ev, Denis S</creatorcontrib><creatorcontrib>Van der Eycken, Erik V</creatorcontrib><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>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Modha, Sachin G</au><au>Trivedi, Jalpa C</au><au>Mehta, Vaibhav P</au><au>Ermolat’ev, Denis S</au><au>Van der Eycken, Erik V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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| ispartof | Journal of organic chemistry, 2011-02, Vol.76 (3), p.846-856 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Base Sequence Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Magnetic Resonance Spectroscopy Microwaves Molecular Structure Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties Pyrazines - chemical synthesis Pyrazines - chemistry Triazoles - chemistry |
| title | An Expeditious Route toward Pyrazine-Containing Nucleoside Analogues |
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