Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions
Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones (indazoledione derivatives). Distinctive features of this protocol include the us...
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| Veröffentlicht in: | Chemistry : a European journal 2019-11, Vol.25 (66), p.15050-15054 |
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| container_issue | 66 |
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| container_title | Chemistry : a European journal |
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| creator | Ortiz‐Rojano, Laura Rojas‐Martín, Jaime Rodríguez‐Diaz, Ciro Carreño, M. Carmen Ribagorda, Maria |
| description | Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones (indazoledione derivatives). Distinctive features of this protocol include the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields. Photophysical and electrochemical properties of the quinones and their potential application as photoredox catalysts are also detailed.
Go photo! Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones. This protocol includes the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields (see scheme). |
| doi_str_mv | 10.1002/chem.201904138 |
| format | Article |
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Go photo! Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones. This protocol includes the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201904138</identifier><identifier>PMID: 31585021</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>1,3-dipolar cycloaddition ; 2,5-diaryltetrazoles ; Catalysts ; Chemistry ; Cycloaddition ; Electrochemical analysis ; Electrochemistry ; photocatalysts ; photoclick ; Pyrazole ; Quinones ; Reagents ; Tetrazoles</subject><ispartof>Chemistry : a European journal, 2019-11, Vol.25 (66), p.15050-15054</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4108-583be91c66d4fc9ed9b1242dc88911b303c292e7d7b0aa029cdf6c73aa7dc03e3</citedby><cites>FETCH-LOGICAL-c4108-583be91c66d4fc9ed9b1242dc88911b303c292e7d7b0aa029cdf6c73aa7dc03e3</cites><orcidid>0000-0002-1721-9936 ; 0000-0001-7185-4095 ; 0000-0003-3741-4840</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201904138$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201904138$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31585021$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ortiz‐Rojano, Laura</creatorcontrib><creatorcontrib>Rojas‐Martín, Jaime</creatorcontrib><creatorcontrib>Rodríguez‐Diaz, Ciro</creatorcontrib><creatorcontrib>Carreño, M. Carmen</creatorcontrib><creatorcontrib>Ribagorda, Maria</creatorcontrib><title>Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones (indazoledione derivatives). Distinctive features of this protocol include the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields. Photophysical and electrochemical properties of the quinones and their potential application as photoredox catalysts are also detailed.
Go photo! Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones. This protocol includes the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields (see scheme).</description><subject>1,3-dipolar cycloaddition</subject><subject>2,5-diaryltetrazoles</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Cycloaddition</subject><subject>Electrochemical analysis</subject><subject>Electrochemistry</subject><subject>photocatalysts</subject><subject>photoclick</subject><subject>Pyrazole</subject><subject>Quinones</subject><subject>Reagents</subject><subject>Tetrazoles</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LAzEQQIMotlavHqXgxYNbZ5L9yk1Zqy1URKjnJZtk7Zbtpm52kXryJ_gb_SWmtFbw4ilMePMYHiGnCAMEoFdyphcDCsjBRxbvkS4GFD0WhcE-6QL3Iy8MGO-QI2vnAMBDxg5Jh2EQB0CxS64nxcus-fr4HFeqlVr1p7qpxbsptft7aovKVLqPl8xNt8XSlKLuJytZGqFU0RSmssfkIBel1Sfbt0ee74bTZORNHu_Hyc3Ekz5C7AUxyzRHGYbKzyXXimdIfapkHHPEjAGTlFMdqSgDIYByqfJQRkyISElgmvXIxca7rM1rq22TLgordVmKSpvWppQB-j5SHjn0_A86N21dueschXEUMxfGUYMNJWtjba3zdFkXC1GvUoR03TZdt013bd3C2VbbZgutdvhPTAfwDfBWlHr1jy5NRsOHX_k3bYeHJA</recordid><startdate>20191127</startdate><enddate>20191127</enddate><creator>Ortiz‐Rojano, Laura</creator><creator>Rojas‐Martín, Jaime</creator><creator>Rodríguez‐Diaz, Ciro</creator><creator>Carreño, M. Carmen</creator><creator>Ribagorda, Maria</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-1721-9936</orcidid><orcidid>https://orcid.org/0000-0001-7185-4095</orcidid><orcidid>https://orcid.org/0000-0003-3741-4840</orcidid></search><sort><creationdate>20191127</creationdate><title>Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions</title><author>Ortiz‐Rojano, Laura ; Rojas‐Martín, Jaime ; Rodríguez‐Diaz, Ciro ; Carreño, M. Carmen ; Ribagorda, Maria</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4108-583be91c66d4fc9ed9b1242dc88911b303c292e7d7b0aa029cdf6c73aa7dc03e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>1,3-dipolar cycloaddition</topic><topic>2,5-diaryltetrazoles</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Cycloaddition</topic><topic>Electrochemical analysis</topic><topic>Electrochemistry</topic><topic>photocatalysts</topic><topic>photoclick</topic><topic>Pyrazole</topic><topic>Quinones</topic><topic>Reagents</topic><topic>Tetrazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ortiz‐Rojano, Laura</creatorcontrib><creatorcontrib>Rojas‐Martín, Jaime</creatorcontrib><creatorcontrib>Rodríguez‐Diaz, Ciro</creatorcontrib><creatorcontrib>Carreño, M. Carmen</creatorcontrib><creatorcontrib>Ribagorda, Maria</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ortiz‐Rojano, Laura</au><au>Rojas‐Martín, Jaime</au><au>Rodríguez‐Diaz, Ciro</au><au>Carreño, M. Carmen</au><au>Ribagorda, Maria</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-11-27</date><risdate>2019</risdate><volume>25</volume><issue>66</issue><spage>15050</spage><epage>15054</epage><pages>15050-15054</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones (indazoledione derivatives). Distinctive features of this protocol include the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields. Photophysical and electrochemical properties of the quinones and their potential application as photoredox catalysts are also detailed.
Go photo! Quinones were firstly used as dipolarophiles in a photoclick 1,3‐cycloaddition with 2,5‐diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole‐fused quinones. This protocol includes the use of light as the unique reagent and readily available, stable, and easy to handle starting materials and good to excellent yields (see scheme).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31585021</pmid><doi>10.1002/chem.201904138</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1721-9936</orcidid><orcidid>https://orcid.org/0000-0001-7185-4095</orcidid><orcidid>https://orcid.org/0000-0003-3741-4840</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 1,3-dipolar cycloaddition 2,5-diaryltetrazoles Catalysts Chemistry Cycloaddition Electrochemical analysis Electrochemistry photocatalysts photoclick Pyrazole Quinones Reagents Tetrazoles |
| title | Light‐Induced Tetrazole‐Quinone 1,3‐Dipolar Cycloadditions |
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