Vinylation of α‑Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5‑a]pyrimidines with a Nonsubstituted Ethylidene Fragment
A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent a...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2021-04, Vol.23 (7), p.2664-2669 |
|---|---|
| Hauptverfasser: | , , , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2669 |
|---|---|
| container_issue | 7 |
| container_start_page | 2664 |
| container_title | Organic letters |
| container_volume | 23 |
| creator | Gao, Qinghe Sun, Zhenhua Xia, Qinfei Li, Ruonan Wang, Wenlong Ma, Siwei Chai, Yixin Wu, Manman Hu, Wei Ábrányi-Balogh, Péter Keserű, György M Han, Xinya |
| description | A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon. |
| doi_str_mv | 10.1021/acs.orglett.1c00571 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2502808861</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2502808861</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-d92424a62d3c107a2088cf0f725022ce8132a3c1f29a03aa2ab3613dd24855023</originalsourceid><addsrcrecordid>eNp9kctKAzEUhoMoXqpPIEiWLmyby0xn6m4oWoWiCy8bkeF0JlMjM5OaZJC68hXc-B6-iA_hk3hKxy6FQELyf184_IQcctbjTPA-ZK5n7KxU3vd4xlgY8Q2yy0MhuxELxeb6PGA7ZM-5Z8Y43gy3yY6UEa54sEs-73W9KMFrU1NT0O-vn_ePpNK1gTdTKkdftX-it1Yr_4QxfFCnNKFjVSsLJb3xFryaLag3dGRq522TeZogah74SYgueJwvrK50jmRrA3qF0WbqvPaNVzk9W7p1jk56bmFWqdrvk60CSqcO2r1D7s7PbkcX3cn1-HKUTLogg9B386EIRAADkcuMswgEi-OsYEUkQiZEpmIuBeBTIYbAJICAqRxwmeciiEOMyA45Xnnn1rw0yvm00i5TZQm1Mo1Ll54YpQh1iFxFM2ucs6pI5zgY2EXKWbosJMVC0raQtC0EqaP2g2ZaqXzN_DWAgf4qsKSfTWNrnPdf5S8Amp72</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2502808861</pqid></control><display><type>article</type><title>Vinylation of α‑Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5‑a]pyrimidines with a Nonsubstituted Ethylidene Fragment</title><source>ACS Publications</source><creator>Gao, Qinghe ; Sun, Zhenhua ; Xia, Qinfei ; Li, Ruonan ; Wang, Wenlong ; Ma, Siwei ; Chai, Yixin ; Wu, Manman ; Hu, Wei ; Ábrányi-Balogh, Péter ; Keserű, György M ; Han, Xinya</creator><creatorcontrib>Gao, Qinghe ; Sun, Zhenhua ; Xia, Qinfei ; Li, Ruonan ; Wang, Wenlong ; Ma, Siwei ; Chai, Yixin ; Wu, Manman ; Hu, Wei ; Ábrányi-Balogh, Péter ; Keserű, György M ; Han, Xinya</creatorcontrib><description>A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.1c00571</identifier><identifier>PMID: 33733786</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2021-04, Vol.23 (7), p.2664-2669</ispartof><rights>2021 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-d92424a62d3c107a2088cf0f725022ce8132a3c1f29a03aa2ab3613dd24855023</citedby><cites>FETCH-LOGICAL-a345t-d92424a62d3c107a2088cf0f725022ce8132a3c1f29a03aa2ab3613dd24855023</cites><orcidid>0000-0002-6207-8933</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/acs.orglett.1c00571$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.1c00571$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33733786$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gao, Qinghe</creatorcontrib><creatorcontrib>Sun, Zhenhua</creatorcontrib><creatorcontrib>Xia, Qinfei</creatorcontrib><creatorcontrib>Li, Ruonan</creatorcontrib><creatorcontrib>Wang, Wenlong</creatorcontrib><creatorcontrib>Ma, Siwei</creatorcontrib><creatorcontrib>Chai, Yixin</creatorcontrib><creatorcontrib>Wu, Manman</creatorcontrib><creatorcontrib>Hu, Wei</creatorcontrib><creatorcontrib>Ábrányi-Balogh, Péter</creatorcontrib><creatorcontrib>Keserű, György M</creatorcontrib><creatorcontrib>Han, Xinya</creatorcontrib><title>Vinylation of α‑Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5‑a]pyrimidines with a Nonsubstituted Ethylidene Fragment</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kctKAzEUhoMoXqpPIEiWLmyby0xn6m4oWoWiCy8bkeF0JlMjM5OaZJC68hXc-B6-iA_hk3hKxy6FQELyf184_IQcctbjTPA-ZK5n7KxU3vd4xlgY8Q2yy0MhuxELxeb6PGA7ZM-5Z8Y43gy3yY6UEa54sEs-73W9KMFrU1NT0O-vn_ePpNK1gTdTKkdftX-it1Yr_4QxfFCnNKFjVSsLJb3xFryaLag3dGRq522TeZogah74SYgueJwvrK50jmRrA3qF0WbqvPaNVzk9W7p1jk56bmFWqdrvk60CSqcO2r1D7s7PbkcX3cn1-HKUTLogg9B386EIRAADkcuMswgEi-OsYEUkQiZEpmIuBeBTIYbAJICAqRxwmeciiEOMyA45Xnnn1rw0yvm00i5TZQm1Mo1Ll54YpQh1iFxFM2ucs6pI5zgY2EXKWbosJMVC0raQtC0EqaP2g2ZaqXzN_DWAgf4qsKSfTWNrnPdf5S8Amp72</recordid><startdate>20210402</startdate><enddate>20210402</enddate><creator>Gao, Qinghe</creator><creator>Sun, Zhenhua</creator><creator>Xia, Qinfei</creator><creator>Li, Ruonan</creator><creator>Wang, Wenlong</creator><creator>Ma, Siwei</creator><creator>Chai, Yixin</creator><creator>Wu, Manman</creator><creator>Hu, Wei</creator><creator>Ábrányi-Balogh, Péter</creator><creator>Keserű, György M</creator><creator>Han, Xinya</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6207-8933</orcidid></search><sort><creationdate>20210402</creationdate><title>Vinylation of α‑Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5‑a]pyrimidines with a Nonsubstituted Ethylidene Fragment</title><author>Gao, Qinghe ; Sun, Zhenhua ; Xia, Qinfei ; Li, Ruonan ; Wang, Wenlong ; Ma, Siwei ; Chai, Yixin ; Wu, Manman ; Hu, Wei ; Ábrányi-Balogh, Péter ; Keserű, György M ; Han, Xinya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-d92424a62d3c107a2088cf0f725022ce8132a3c1f29a03aa2ab3613dd24855023</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gao, Qinghe</creatorcontrib><creatorcontrib>Sun, Zhenhua</creatorcontrib><creatorcontrib>Xia, Qinfei</creatorcontrib><creatorcontrib>Li, Ruonan</creatorcontrib><creatorcontrib>Wang, Wenlong</creatorcontrib><creatorcontrib>Ma, Siwei</creatorcontrib><creatorcontrib>Chai, Yixin</creatorcontrib><creatorcontrib>Wu, Manman</creatorcontrib><creatorcontrib>Hu, Wei</creatorcontrib><creatorcontrib>Ábrányi-Balogh, Péter</creatorcontrib><creatorcontrib>Keserű, György M</creatorcontrib><creatorcontrib>Han, Xinya</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gao, Qinghe</au><au>Sun, Zhenhua</au><au>Xia, Qinfei</au><au>Li, Ruonan</au><au>Wang, Wenlong</au><au>Ma, Siwei</au><au>Chai, Yixin</au><au>Wu, Manman</au><au>Hu, Wei</au><au>Ábrányi-Balogh, Péter</au><au>Keserű, György M</au><au>Han, Xinya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Vinylation of α‑Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5‑a]pyrimidines with a Nonsubstituted Ethylidene Fragment</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2021-04-02</date><risdate>2021</risdate><volume>23</volume><issue>7</issue><spage>2664</spage><epage>2669</epage><pages>2664-2669</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>33733786</pmid><doi>10.1021/acs.orglett.1c00571</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-6207-8933</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2021-04, Vol.23 (7), p.2664-2669 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2502808861 |
| source | ACS Publications |
| title | Vinylation of α‑Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5‑a]pyrimidines with a Nonsubstituted Ethylidene Fragment |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-10T08%3A25%3A30IST&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=Vinylation%20of%20%CE%B1%E2%80%91Aminoazoles%20with%20Triethylamine:%20A%20General%20Strategy%20to%20Construct%20Azolo%5B1,5%E2%80%91a%5Dpyrimidines%20with%20a%20Nonsubstituted%20Ethylidene%20Fragment&rft.jtitle=Organic%20letters&rft.au=Gao,%20Qinghe&rft.date=2021-04-02&rft.volume=23&rft.issue=7&rft.spage=2664&rft.epage=2669&rft.pages=2664-2669&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.1c00571&rft_dat=%3Cproquest_cross%3E2502808861%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=2502808861&rft_id=info:pmid/33733786&rfr_iscdi=true |