Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives
•Unexpected isomers were synthesized by 1,3-dipolar cycloaddition reaction of DPNI.•The structures of products were solved by single crystal X-ray analysis.•A cycloaddition/ring-opening/rearrangement mechanism was proposed. 1,3-Dipolar cycloaddition of 2-arylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrim...
Gespeichert in:
| Veröffentlicht in: | Tetrahedron letters 2013-12, Vol.54 (50), p.6952-6954 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 6954 |
|---|---|
| container_issue | 50 |
| container_start_page | 6952 |
| container_title | Tetrahedron letters |
| container_volume | 54 |
| creator | Liu, Bin Li, Xiao-Fang Liu, Hao-Chong Yu, Xian-Yong |
| description | •Unexpected isomers were synthesized by 1,3-dipolar cycloaddition reaction of DPNI.•The structures of products were solved by single crystal X-ray analysis.•A cycloaddition/ring-opening/rearrangement mechanism was proposed.
1,3-Dipolar cycloaddition of 2-arylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-3(5H)-ones to diphenylnitrilimine (generated in situ by triethylamine dehydrohalogenation of the N′-phenylbenzohydrazonoyl chloride) proceeded regio- and site-selectively affording a mixture of two unexpected isomer products at reflux temperature. The cycloaddition/ring-opening/rearrangement/substitution, mechanism of the reaction was also discussed. |
| doi_str_mv | 10.1016/j.tetlet.2013.10.062 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744709774</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040403913017978</els_id><sourcerecordid>1744709774</sourcerecordid><originalsourceid>FETCH-LOGICAL-c479t-4440081100d6229d1ed4252316280697e2268a5445a51a1e1df66f0edeaece103</originalsourceid><addsrcrecordid>eNp9kE9LxDAQxYMouK5-Aw89erB1kqZpexFk8R-seHFPIiEkU8zSbdYku7h-elPq2bkMPN57zPwIuaRQUKDiZl1EjD3GggEtk1SAYEdkRpu6zMuqocdkBsAh51C2p-QshDWkEQ3MyMtqwO8t6ogmG2z0trcbO2CmD7p3yhgbrRsy12Xx06of17v38prl6mN78MloRqtBb_cq2j2Gc3LSqT7gxd-ek9XD_dviKV--Pj4v7pa55nUbc845QEMpgBGMtYai4axiJRWsAdHWyJhoVMV5pSqqKFLTCdEBGlSokUI5J1dT79a7rx2GKDc2aOx7NaDbBUlrzmto65onK5-s2rsQPHZymy5X_iApyJGeXMuJnhzpjWqil2K3UwzTG3uLXgZtcdBorE-0pHH2_4JfLVF6hA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744709774</pqid></control><display><type>article</type><title>Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives</title><source>Elsevier ScienceDirect Journals Complete</source><creator>Liu, Bin ; Li, Xiao-Fang ; Liu, Hao-Chong ; Yu, Xian-Yong</creator><creatorcontrib>Liu, Bin ; Li, Xiao-Fang ; Liu, Hao-Chong ; Yu, Xian-Yong</creatorcontrib><description>•Unexpected isomers were synthesized by 1,3-dipolar cycloaddition reaction of DPNI.•The structures of products were solved by single crystal X-ray analysis.•A cycloaddition/ring-opening/rearrangement mechanism was proposed.
1,3-Dipolar cycloaddition of 2-arylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-3(5H)-ones to diphenylnitrilimine (generated in situ by triethylamine dehydrohalogenation of the N′-phenylbenzohydrazonoyl chloride) proceeded regio- and site-selectively affording a mixture of two unexpected isomer products at reflux temperature. The cycloaddition/ring-opening/rearrangement/substitution, mechanism of the reaction was also discussed.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2013.10.062</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>1,3-Dipolar cycloaddition ; Chlorides ; Cycloaddition ; Derivatives ; Diphenylnitrilimine ; Isomers ; Pyrrolo[1,2-a][1,2,4]triazolo[3,4-b]pyrimidine ; Tetrahedrons ; Thiazolo[3,2-a][1,2,4]triazolo[3,4-b]pyrimidine ; Thiazolo[3,2-a]pyrimidine ; Triethylamine</subject><ispartof>Tetrahedron letters, 2013-12, Vol.54 (50), p.6952-6954</ispartof><rights>2013 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c479t-4440081100d6229d1ed4252316280697e2268a5445a51a1e1df66f0edeaece103</citedby><cites>FETCH-LOGICAL-c479t-4440081100d6229d1ed4252316280697e2268a5445a51a1e1df66f0edeaece103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2013.10.062$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Liu, Bin</creatorcontrib><creatorcontrib>Li, Xiao-Fang</creatorcontrib><creatorcontrib>Liu, Hao-Chong</creatorcontrib><creatorcontrib>Yu, Xian-Yong</creatorcontrib><title>Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives</title><title>Tetrahedron letters</title><description>•Unexpected isomers were synthesized by 1,3-dipolar cycloaddition reaction of DPNI.•The structures of products were solved by single crystal X-ray analysis.•A cycloaddition/ring-opening/rearrangement mechanism was proposed.
1,3-Dipolar cycloaddition of 2-arylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-3(5H)-ones to diphenylnitrilimine (generated in situ by triethylamine dehydrohalogenation of the N′-phenylbenzohydrazonoyl chloride) proceeded regio- and site-selectively affording a mixture of two unexpected isomer products at reflux temperature. The cycloaddition/ring-opening/rearrangement/substitution, mechanism of the reaction was also discussed.</description><subject>1,3-Dipolar cycloaddition</subject><subject>Chlorides</subject><subject>Cycloaddition</subject><subject>Derivatives</subject><subject>Diphenylnitrilimine</subject><subject>Isomers</subject><subject>Pyrrolo[1,2-a][1,2,4]triazolo[3,4-b]pyrimidine</subject><subject>Tetrahedrons</subject><subject>Thiazolo[3,2-a][1,2,4]triazolo[3,4-b]pyrimidine</subject><subject>Thiazolo[3,2-a]pyrimidine</subject><subject>Triethylamine</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kE9LxDAQxYMouK5-Aw89erB1kqZpexFk8R-seHFPIiEkU8zSbdYku7h-elPq2bkMPN57zPwIuaRQUKDiZl1EjD3GggEtk1SAYEdkRpu6zMuqocdkBsAh51C2p-QshDWkEQ3MyMtqwO8t6ogmG2z0trcbO2CmD7p3yhgbrRsy12Xx06of17v38prl6mN78MloRqtBb_cq2j2Gc3LSqT7gxd-ek9XD_dviKV--Pj4v7pa55nUbc845QEMpgBGMtYai4axiJRWsAdHWyJhoVMV5pSqqKFLTCdEBGlSokUI5J1dT79a7rx2GKDc2aOx7NaDbBUlrzmto65onK5-s2rsQPHZymy5X_iApyJGeXMuJnhzpjWqil2K3UwzTG3uLXgZtcdBorE-0pHH2_4JfLVF6hA</recordid><startdate>20131211</startdate><enddate>20131211</enddate><creator>Liu, Bin</creator><creator>Li, Xiao-Fang</creator><creator>Liu, Hao-Chong</creator><creator>Yu, Xian-Yong</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20131211</creationdate><title>Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives</title><author>Liu, Bin ; Li, Xiao-Fang ; Liu, Hao-Chong ; Yu, Xian-Yong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c479t-4440081100d6229d1ed4252316280697e2268a5445a51a1e1df66f0edeaece103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>1,3-Dipolar cycloaddition</topic><topic>Chlorides</topic><topic>Cycloaddition</topic><topic>Derivatives</topic><topic>Diphenylnitrilimine</topic><topic>Isomers</topic><topic>Pyrrolo[1,2-a][1,2,4]triazolo[3,4-b]pyrimidine</topic><topic>Tetrahedrons</topic><topic>Thiazolo[3,2-a][1,2,4]triazolo[3,4-b]pyrimidine</topic><topic>Thiazolo[3,2-a]pyrimidine</topic><topic>Triethylamine</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Bin</creatorcontrib><creatorcontrib>Li, Xiao-Fang</creatorcontrib><creatorcontrib>Liu, Hao-Chong</creatorcontrib><creatorcontrib>Yu, Xian-Yong</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Bin</au><au>Li, Xiao-Fang</au><au>Liu, Hao-Chong</au><au>Yu, Xian-Yong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives</atitle><jtitle>Tetrahedron letters</jtitle><date>2013-12-11</date><risdate>2013</risdate><volume>54</volume><issue>50</issue><spage>6952</spage><epage>6954</epage><pages>6952-6954</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>•Unexpected isomers were synthesized by 1,3-dipolar cycloaddition reaction of DPNI.•The structures of products were solved by single crystal X-ray analysis.•A cycloaddition/ring-opening/rearrangement mechanism was proposed.
1,3-Dipolar cycloaddition of 2-arylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidine-3(5H)-ones to diphenylnitrilimine (generated in situ by triethylamine dehydrohalogenation of the N′-phenylbenzohydrazonoyl chloride) proceeded regio- and site-selectively affording a mixture of two unexpected isomer products at reflux temperature. The cycloaddition/ring-opening/rearrangement/substitution, mechanism of the reaction was also discussed.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2013.10.062</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4039 |
| ispartof | Tetrahedron letters, 2013-12, Vol.54 (50), p.6952-6954 |
| issn | 0040-4039 1873-3581 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1744709774 |
| source | Elsevier ScienceDirect Journals Complete |
| subjects | 1,3-Dipolar cycloaddition Chlorides Cycloaddition Derivatives Diphenylnitrilimine Isomers Pyrrolo[1,2-a][1,2,4]triazolo[3,4-b]pyrimidine Tetrahedrons Thiazolo[3,2-a][1,2,4]triazolo[3,4-b]pyrimidine Thiazolo[3,2-a]pyrimidine Triethylamine |
| title | Unexpected nitrilimine cycloaddition of thiazolo[3,2-a]pyrimidine derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T14%3A16%3A24IST&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=Unexpected%20nitrilimine%20cycloaddition%20of%20thiazolo%5B3,2-a%5Dpyrimidine%20derivatives&rft.jtitle=Tetrahedron%20letters&rft.au=Liu,%20Bin&rft.date=2013-12-11&rft.volume=54&rft.issue=50&rft.spage=6952&rft.epage=6954&rft.pages=6952-6954&rft.issn=0040-4039&rft.eissn=1873-3581&rft_id=info:doi/10.1016/j.tetlet.2013.10.062&rft_dat=%3Cproquest_cross%3E1744709774%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=1744709774&rft_id=info:pmid/&rft_els_id=S0040403913017978&rfr_iscdi=true |