A Simple, Modular Method for the Synthesis of 3,4,5-Trisubstituted Pyrazoles
A modular approach for the regiocontrolled preparation of pyrazoles bearing substituents on all three carbon atoms is described. Central to this method is the use of a switchable metal-directing group (MDG) to enable sequential direct lithiation of the 3- and 5-positions of the pyrazole ring. Pyrazo...
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| Veröffentlicht in: | Journal of organic chemistry 2008-06, Vol.73 (11), p.4309-4312 |
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| container_end_page | 4312 |
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| container_issue | 11 |
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| container_title | Journal of organic chemistry |
| container_volume | 73 |
| creator | McLaughlin, Mark Marcantonio, Karen Chen, Cheng-yi Davies, Ian W |
| description | A modular approach for the regiocontrolled preparation of pyrazoles bearing substituents on all three carbon atoms is described. Central to this method is the use of a switchable metal-directing group (MDG) to enable sequential direct lithiation of the 3- and 5-positions of the pyrazole ring. Pyrazole boronic esters obtained from these lithiated intermediates can undergo efficient Suzuki cross-coupling under the developed nonaqueous conditions, which minimize undesirable protolytic deboronation. Halogenation of the 4-position provides the means for substitution at the remaining carbon atom. |
| doi_str_mv | 10.1021/jo800321p |
| format | Article |
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Org. Chem</addtitle><description>A modular approach for the regiocontrolled preparation of pyrazoles bearing substituents on all three carbon atoms is described. Central to this method is the use of a switchable metal-directing group (MDG) to enable sequential direct lithiation of the 3- and 5-positions of the pyrazole ring. Pyrazole boronic esters obtained from these lithiated intermediates can undergo efficient Suzuki cross-coupling under the developed nonaqueous conditions, which minimize undesirable protolytic deboronation. Halogenation of the 4-position provides the means for substitution at the remaining carbon atom.</description><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>Mass Spectrometry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkD1PwzAQhi0EglIY-APIC0hIDdiOnThj-UYqolLLwmI5yVkE0rr4Eony6wlq1S7c8g736L3TQ8gJZ5ecCX714TVjseCLHdLjSrAoyZjcJT3GhIhikcQH5BDxg3WjlNonB1xLKRMtemQ0pJNqtqhhQJ992dY20Gdo3n1JnQ-0eQc6Wc67wAqpdzQeyIGKpqHCNsematoGSjpeBvvja8AjsudsjXC8zj55vb-b3jxGo5eHp5vhKLJSpk2ksjROZK7zMhO5K51KuVWq4InjCSvTXLMMhJNMiVyCtgUHcFDmItNOC-dU3Cfnq95F8F8tYGNmFRZQ13YOvkWT8oTLTGUdeLECi-ARAzizCNXMhqXhzPypMxt1HXu6Lm3zGZRbcu2qA87WgMXC1i7YeVHhhhMs1jpjf0ejFVdhA9-bvQ2fJknjVJnpeGLG-vr2bSKYSbe9tsDunzbMO3f_PPgLlwKQHw</recordid><startdate>20080606</startdate><enddate>20080606</enddate><creator>McLaughlin, Mark</creator><creator>Marcantonio, Karen</creator><creator>Chen, Cheng-yi</creator><creator>Davies, Ian W</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20080606</creationdate><title>A Simple, Modular Method for the Synthesis of 3,4,5-Trisubstituted Pyrazoles</title><author>McLaughlin, Mark ; Marcantonio, Karen ; Chen, Cheng-yi ; Davies, Ian W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a447t-597364b8bd92bfdf571a55c16f160d7b809e2f4052b4e8ac1eefedb298f82ff53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><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>Mass Spectrometry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McLaughlin, Mark</creatorcontrib><creatorcontrib>Marcantonio, Karen</creatorcontrib><creatorcontrib>Chen, Cheng-yi</creatorcontrib><creatorcontrib>Davies, Ian W</creatorcontrib><collection>Istex</collection><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>McLaughlin, Mark</au><au>Marcantonio, Karen</au><au>Chen, Cheng-yi</au><au>Davies, Ian W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Simple, Modular Method for the Synthesis of 3,4,5-Trisubstituted Pyrazoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2008-06-06</date><risdate>2008</risdate><volume>73</volume><issue>11</issue><spage>4309</spage><epage>4312</epage><pages>4309-4312</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A modular approach for the regiocontrolled preparation of pyrazoles bearing substituents on all three carbon atoms is described. Central to this method is the use of a switchable metal-directing group (MDG) to enable sequential direct lithiation of the 3- and 5-positions of the pyrazole ring. Pyrazole boronic esters obtained from these lithiated intermediates can undergo efficient Suzuki cross-coupling under the developed nonaqueous conditions, which minimize undesirable protolytic deboronation. Halogenation of the 4-position provides the means for substitution at the remaining carbon atom.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18444682</pmid><doi>10.1021/jo800321p</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2008-06, Vol.73 (11), p.4309-4312 |
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| source | ACS Publications; MEDLINE |
| subjects | 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 Mass Spectrometry Organic chemistry Preparations and properties Pyrazoles - chemical synthesis Pyrazoles - chemistry Spectrometry, Mass, Electrospray Ionization |
| title | A Simple, Modular Method for the Synthesis of 3,4,5-Trisubstituted Pyrazoles |
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