Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]- pyrimidine regioisomers by 1H15N HMBC experiments
The condensation of malonoaldehyde derivatives with either a 3‐amino‐[1,2,4]‐triazole or a 3,5‐diamino‐[1,2,4]‐triazole precursor was studied. In agreement with previous reports, two different bicycles, namely, bearing the regioisomeric [1,2,4]triazolo[1,5‐a]pyrimidine (1) or[1,2,4] triazolo [4,3‐a]...
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| Veröffentlicht in: | Magnetic resonance in chemistry 2010-08, Vol.48 (8), p.614-622 |
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| creator | Salgado, Antonio Varela, Carmen García Collazo, Ana María Pevarello, Paolo |
| description | The condensation of malonoaldehyde derivatives with either a 3‐amino‐[1,2,4]‐triazole or a 3,5‐diamino‐[1,2,4]‐triazole precursor was studied. In agreement with previous reports, two different bicycles, namely, bearing the regioisomeric [1,2,4]triazolo[1,5‐a]pyrimidine (1) or[1,2,4] triazolo [4,3‐a]pyrimidine (2) structural surrogates, could be obtained. We found that, depending on the triazole precursor, only one regioisomer resulted, either of the 1 or 2 series. We also observed that these two structural surrogates could be unambiguously differentiated by indirectly measuring their 15N chemical shifts by 1H15N HMBC experiments. The occasional conversion of [1,2,4]triazolo[4,3‐a]pyrimidines to the [1,2,4]triazolo[1,5‐a]pyrimidine counterparts could be unequivocally determined by 15N NMR data. Copyright © 2010 John Wiley & Sons, Ltd.
Regioisomeric [1,2,4]triazolo[1,5‐a] pyrimidine (1) and [1,2,4]triazolo[4,3‐a]pyrimidine derivatives (2), respec‐ tively obtained by condensation of malonoaldehydes with 3‐amino‐ [1,2,4]‐triazole or 3,5‐diamino‐[1,2,4]‐ triazole precursors, were unambiguously characterized by 1H15N HMBC experiments. |
| doi_str_mv | 10.1002/mrc.2634 |
| format | Article |
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Regioisomeric [1,2,4]triazolo[1,5‐a] pyrimidine (1) and [1,2,4]triazolo[4,3‐a]pyrimidine derivatives (2), respec‐ tively obtained by condensation of malonoaldehydes with 3‐amino‐ [1,2,4]‐triazole or 3,5‐diamino‐[1,2,4]‐ triazole precursors, were unambiguously characterized by 1H15N HMBC experiments.</description><identifier>ISSN: 0749-1581</identifier><identifier>EISSN: 1097-458X</identifier><identifier>DOI: 10.1002/mrc.2634</identifier><identifier>PMID: 20589727</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>13C ; 15N ; 3-a]pyrimidines ; 4]triazolo ; 5-a]pyrimidines ; [1,2,4]triazolo[1,5‐a]pyrimidines ; [1,2,4]triazolo[4,3‐a]pyrimidines ; HMBC ; isomerisation ; Magnetic Resonance Spectroscopy - standards ; Molecular Structure ; Nitrogen Isotopes ; NMR ; Protons ; Pyrimidines - chemistry ; Reference Standards ; regioisomerism ; Stereoisomerism ; Triazoles - chemistry</subject><ispartof>Magnetic resonance in chemistry, 2010-08, Vol.48 (8), p.614-622</ispartof><rights>Copyright © 2010 John Wiley & Sons, Ltd.</rights><rights>2010 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fmrc.2634$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmrc.2634$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20589727$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Salgado, Antonio</creatorcontrib><creatorcontrib>Varela, Carmen</creatorcontrib><creatorcontrib>García Collazo, Ana María</creatorcontrib><creatorcontrib>Pevarello, Paolo</creatorcontrib><title>Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]- pyrimidine regioisomers by 1H15N HMBC experiments</title><title>Magnetic resonance in chemistry</title><addtitle>Magn. Reson. Chem</addtitle><description>The condensation of malonoaldehyde derivatives with either a 3‐amino‐[1,2,4]‐triazole or a 3,5‐diamino‐[1,2,4]‐triazole precursor was studied. In agreement with previous reports, two different bicycles, namely, bearing the regioisomeric [1,2,4]triazolo[1,5‐a]pyrimidine (1) or[1,2,4] triazolo [4,3‐a]pyrimidine (2) structural surrogates, could be obtained. We found that, depending on the triazole precursor, only one regioisomer resulted, either of the 1 or 2 series. We also observed that these two structural surrogates could be unambiguously differentiated by indirectly measuring their 15N chemical shifts by 1H15N HMBC experiments. The occasional conversion of [1,2,4]triazolo[4,3‐a]pyrimidines to the [1,2,4]triazolo[1,5‐a]pyrimidine counterparts could be unequivocally determined by 15N NMR data. Copyright © 2010 John Wiley & Sons, Ltd.
Regioisomeric [1,2,4]triazolo[1,5‐a] pyrimidine (1) and [1,2,4]triazolo[4,3‐a]pyrimidine derivatives (2), respec‐ tively obtained by condensation of malonoaldehydes with 3‐amino‐ [1,2,4]‐triazole or 3,5‐diamino‐[1,2,4]‐ triazole precursors, were unambiguously characterized by 1H15N HMBC experiments.</description><subject>13C</subject><subject>15N</subject><subject>3-a]pyrimidines</subject><subject>4]triazolo</subject><subject>5-a]pyrimidines</subject><subject>[1,2,4]triazolo[1,5‐a]pyrimidines</subject><subject>[1,2,4]triazolo[4,3‐a]pyrimidines</subject><subject>HMBC</subject><subject>isomerisation</subject><subject>Magnetic Resonance Spectroscopy - standards</subject><subject>Molecular Structure</subject><subject>Nitrogen Isotopes</subject><subject>NMR</subject><subject>Protons</subject><subject>Pyrimidines - chemistry</subject><subject>Reference Standards</subject><subject>regioisomerism</subject><subject>Stereoisomerism</subject><subject>Triazoles - chemistry</subject><issn>0749-1581</issn><issn>1097-458X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpl0VtKHEEUBuAiROJ4AVcg_ZaXaa375VFn1Ak4ClFRECmqe06HSvoyVvWgkyW4DReSJWUL1qAxgTwdDvVRp-r8CO0QvEcwpvtNKPeoZPwDGhBsVM6FvvmIBlhxkxOhyTraiPE7xtgYxT6hdYqFNoqqAXoa-6qCAG3vXe-7NiugfwBos1sypEN-1wfvfnZ1l1qRu7tsvgy-8TPfQuba2X-KD1lS-b8swDff-dg1EGJWLDMy-f38i4izbDI9HGXwOIdE0_y4hdYqV0fYfqub6Or46HI0yU_PT76MDk5zT4nkuTSMO8WAS2mwkIoJCQak5rwoyrJgGs9YWgIwyisOhlVKEQOkJMZRqYlmm-jz673z0N0vIPa28bGEunYtdItoFWNGU2l4krtvclE0MLPz9FIXlvbP-hLIX8GDr2H5fk6wXcViUyx2FYudfh2t6l_vYw-P796FHzZ9RAl7fXZiBR1P-YXgVrMXZ7qM6g</recordid><startdate>201008</startdate><enddate>201008</enddate><creator>Salgado, Antonio</creator><creator>Varela, Carmen</creator><creator>García Collazo, Ana María</creator><creator>Pevarello, Paolo</creator><general>John Wiley & Sons, Ltd</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>201008</creationdate><title>Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]- pyrimidine regioisomers by 1H15N HMBC experiments</title><author>Salgado, Antonio ; Varela, Carmen ; García Collazo, Ana María ; Pevarello, Paolo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2164-6934a73e46690567356e9e6844bbccb380d3109e324f4e93f7719e1c19a268183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>13C</topic><topic>15N</topic><topic>3-a]pyrimidines</topic><topic>4]triazolo</topic><topic>5-a]pyrimidines</topic><topic>[1,2,4]triazolo[1,5‐a]pyrimidines</topic><topic>[1,2,4]triazolo[4,3‐a]pyrimidines</topic><topic>HMBC</topic><topic>isomerisation</topic><topic>Magnetic Resonance Spectroscopy - standards</topic><topic>Molecular Structure</topic><topic>Nitrogen Isotopes</topic><topic>NMR</topic><topic>Protons</topic><topic>Pyrimidines - chemistry</topic><topic>Reference Standards</topic><topic>regioisomerism</topic><topic>Stereoisomerism</topic><topic>Triazoles - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Salgado, Antonio</creatorcontrib><creatorcontrib>Varela, Carmen</creatorcontrib><creatorcontrib>García Collazo, Ana María</creatorcontrib><creatorcontrib>Pevarello, Paolo</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Magnetic resonance in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Salgado, Antonio</au><au>Varela, Carmen</au><au>García Collazo, Ana María</au><au>Pevarello, Paolo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]- pyrimidine regioisomers by 1H15N HMBC experiments</atitle><jtitle>Magnetic resonance in chemistry</jtitle><addtitle>Magn. Reson. Chem</addtitle><date>2010-08</date><risdate>2010</risdate><volume>48</volume><issue>8</issue><spage>614</spage><epage>622</epage><pages>614-622</pages><issn>0749-1581</issn><eissn>1097-458X</eissn><abstract>The condensation of malonoaldehyde derivatives with either a 3‐amino‐[1,2,4]‐triazole or a 3,5‐diamino‐[1,2,4]‐triazole precursor was studied. In agreement with previous reports, two different bicycles, namely, bearing the regioisomeric [1,2,4]triazolo[1,5‐a]pyrimidine (1) or[1,2,4] triazolo [4,3‐a]pyrimidine (2) structural surrogates, could be obtained. We found that, depending on the triazole precursor, only one regioisomer resulted, either of the 1 or 2 series. We also observed that these two structural surrogates could be unambiguously differentiated by indirectly measuring their 15N chemical shifts by 1H15N HMBC experiments. The occasional conversion of [1,2,4]triazolo[4,3‐a]pyrimidines to the [1,2,4]triazolo[1,5‐a]pyrimidine counterparts could be unequivocally determined by 15N NMR data. Copyright © 2010 John Wiley & Sons, Ltd.
Regioisomeric [1,2,4]triazolo[1,5‐a] pyrimidine (1) and [1,2,4]triazolo[4,3‐a]pyrimidine derivatives (2), respec‐ tively obtained by condensation of malonoaldehydes with 3‐amino‐ [1,2,4]‐triazole or 3,5‐diamino‐[1,2,4]‐ triazole precursors, were unambiguously characterized by 1H15N HMBC experiments.</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>20589727</pmid><doi>10.1002/mrc.2634</doi><tpages>9</tpages></addata></record> |
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| subjects | 13C 15N 3-a]pyrimidines 4]triazolo 5-a]pyrimidines [1,2,4]triazolo[1,5‐a]pyrimidines [1,2,4]triazolo[4,3‐a]pyrimidines HMBC isomerisation Magnetic Resonance Spectroscopy - standards Molecular Structure Nitrogen Isotopes NMR Protons Pyrimidines - chemistry Reference Standards regioisomerism Stereoisomerism Triazoles - chemistry |
| title | Differentiation between [1,2,4]triazolo[1,5-a] pyrimidine and [1,2,4]triazolo[4,3-a]- pyrimidine regioisomers by 1H15N HMBC experiments |
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