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An Efficient One-Pot Synthesis of 3,5-Diaryl-4-bromopyrazoles by 1,3-Dipolar Cycloaddition of In Situ Generated Diazo Compounds and 1-Bromoalk-1-ynes
Abstract A simple, highly efficient, one-pot synthesis of 3,5-diaryl-4-bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and gem -dibromoalkenes, respectively....
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| Published in: | Synthesis (Stuttgart) 2013-02, Vol.45 (3), p.413-420 |
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| Main Authors: | , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c343t-c0ed93869eef4783bab96de55ae665c5830a7fb84f09ffda2f423803f09487543 |
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| container_end_page | 420 |
| container_issue | 3 |
| container_start_page | 413 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 45 |
| creator | Sha, Qiang Wei, Yunyang |
| description | Abstract
A simple, highly efficient, one-pot synthesis of 3,5-diaryl-4-bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and
gem
-dibromoalkenes, respectively. When ketone-derived hydrazones were used, 3,5-diaryl-4-bromo-3
H
-pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1
H
-pyrazoles were formed when using aldehyde-derived hydrazones. The reaction system exhibited high regioselectivity and good functional group tolerance. Both electron-rich and electron-deficient substituents on the aromatic ring of the hydrazones or the
gem
-dibromoalkenes gave desired products in moderate to good yields (67–86%). |
| doi_str_mv | 10.1055/s-0032-1317992 |
| format | article |
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A simple, highly efficient, one-pot synthesis of 3,5-diaryl-4-bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and
gem
-dibromoalkenes, respectively. When ketone-derived hydrazones were used, 3,5-diaryl-4-bromo-3
H
-pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1
H
-pyrazoles were formed when using aldehyde-derived hydrazones. The reaction system exhibited high regioselectivity and good functional group tolerance. Both electron-rich and electron-deficient substituents on the aromatic ring of the hydrazones or the
gem
-dibromoalkenes gave desired products in moderate to good yields (67–86%).</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0032-1317992</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2013-02, Vol.45 (3), p.413-420</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c343t-c0ed93869eef4783bab96de55ae665c5830a7fb84f09ffda2f423803f09487543</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0032-1317992.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0032-1317992$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3004,3005,27900,27901,54533,54534</link.rule.ids></links><search><creatorcontrib>Sha, Qiang</creatorcontrib><creatorcontrib>Wei, Yunyang</creatorcontrib><title>An Efficient One-Pot Synthesis of 3,5-Diaryl-4-bromopyrazoles by 1,3-Dipolar Cycloaddition of In Situ Generated Diazo Compounds and 1-Bromoalk-1-ynes</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
A simple, highly efficient, one-pot synthesis of 3,5-diaryl-4-bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and
gem
-dibromoalkenes, respectively. When ketone-derived hydrazones were used, 3,5-diaryl-4-bromo-3
H
-pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1
H
-pyrazoles were formed when using aldehyde-derived hydrazones. The reaction system exhibited high regioselectivity and good functional group tolerance. Both electron-rich and electron-deficient substituents on the aromatic ring of the hydrazones or the
gem
-dibromoalkenes gave desired products in moderate to good yields (67–86%).</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp1kM1OwzAQhC0EEqVw5ewHqIsd2_k5lgKlUqUiFSRukZOsVZfEjuz0kL4H70ui9spptZqdTzuD0COjc0alfAqEUh4RxlmSZdEVmjDBExIx-n2NJoOUkSRN2S26C-FAKU0ink3Q78LiV61NacB2eGuBfLgO73rb7SGYgJ3GfCbJi1G-r4kghXeNa3uvTq6GgIsesxkf5NbVyuNlX9ZOVZXpjLOjd23xznRHvAILXnVQ4YF0cnjpmtYdbRWwshVm5HnEqvqHMNJbCPfoRqs6wMNlTtHX2-vn8p1stqv1crEhJRe8IyWFKuNpnAFokaS8UEUWVyClgjiWpUw5VYkuUqFppnWlIi0inlI-rCJNpOBTND9zS-9C8KDz1ptmiJozmo-l5iEfS80vpQ4GcjZ0ewMN5Ad39Hb48L_7P7UReGI</recordid><startdate>20130201</startdate><enddate>20130201</enddate><creator>Sha, Qiang</creator><creator>Wei, Yunyang</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130201</creationdate><title>An Efficient One-Pot Synthesis of 3,5-Diaryl-4-bromopyrazoles by 1,3-Dipolar Cycloaddition of In Situ Generated Diazo Compounds and 1-Bromoalk-1-ynes</title><author>Sha, Qiang ; Wei, Yunyang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-c0ed93869eef4783bab96de55ae665c5830a7fb84f09ffda2f423803f09487543</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sha, Qiang</creatorcontrib><creatorcontrib>Wei, Yunyang</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sha, Qiang</au><au>Wei, Yunyang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Efficient One-Pot Synthesis of 3,5-Diaryl-4-bromopyrazoles by 1,3-Dipolar Cycloaddition of In Situ Generated Diazo Compounds and 1-Bromoalk-1-ynes</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2013-02-01</date><risdate>2013</risdate><volume>45</volume><issue>3</issue><spage>413</spage><epage>420</epage><pages>413-420</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
A simple, highly efficient, one-pot synthesis of 3,5-diaryl-4-bromopyrazoles via 1,3-dipolar cycloaddition of diazo compounds and alkynyl bromides has been developed. The diazo compounds and alkynyl bromides were generated in situ from tosylhydrazones and
gem
-dibromoalkenes, respectively. When ketone-derived hydrazones were used, 3,5-diaryl-4-bromo-3
H
-pyrazoles were obtained and the isomerization products 3,5-diaryl-4-bromo-1
H
-pyrazoles were formed when using aldehyde-derived hydrazones. The reaction system exhibited high regioselectivity and good functional group tolerance. Both electron-rich and electron-deficient substituents on the aromatic ring of the hydrazones or the
gem
-dibromoalkenes gave desired products in moderate to good yields (67–86%).</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0032-1317992</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0039-7881 |
| ispartof | Synthesis (Stuttgart), 2013-02, Vol.45 (3), p.413-420 |
| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0032_1317992 |
| source | Thieme Connect Journals |
| title | An Efficient One-Pot Synthesis of 3,5-Diaryl-4-bromopyrazoles by 1,3-Dipolar Cycloaddition of In Situ Generated Diazo Compounds and 1-Bromoalk-1-ynes |
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