Efficient Synthesis and Iodine‐Functionalization of Pyrazoles via KIO3/PhSeSePh System under Acidic Conditions
This manuscript reports a novel method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and various hydrazines. In this approach, potassium iodate (KIO3) is used as the iodinating agent and (PhSe)2 is used as catalysts under acidic c...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2024-12, Vol.19 (23), p.e202400749-n/a |
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| creator | Peglow, Thiago J. Thomaz, João Pedro S. S. C. Nobre, Patrick C. Scimmi, Cecilia Santi, Claudio Nascimento, Vanessa |
| description | This manuscript reports a novel method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and various hydrazines. In this approach, potassium iodate (KIO3) is used as the iodinating agent and (PhSe)2 is used as catalysts under acidic conditions. This protocol provides a convenient method for the efficient synthesis of 4‐iodo‐1‐aryl‐1H‐pyrazoles, valuable intermediates for several different coupling reactions.
We develop a new method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and hydrazines. In this approach, potassium iodate is used as the iodinating agent along with diphenyl diselenide under acidic conditions. The method is simple and efficient and allows the synthesis of 4‐iodopyrazoles and other iodinated heterocycles. |
| doi_str_mv | 10.1002/asia.202400749 |
| format | Article |
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We develop a new method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and hydrazines. In this approach, potassium iodate is used as the iodinating agent along with diphenyl diselenide under acidic conditions. The method is simple and efficient and allows the synthesis of 4‐iodopyrazoles and other iodinated heterocycles.</description><identifier>ISSN: 1861-4728</identifier><identifier>ISSN: 1861-471X</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.202400749</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>catalysis ; Chemical reactions ; Chemical synthesis ; Hydrazines ; Iodination ; Iodine ; N-heterocycles ; Pyrazole ; selenium</subject><ispartof>Chemistry, an Asian journal, 2024-12, Vol.19 (23), p.e202400749-n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><rights>2024 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-7698-8970 ; 0000-0001-9413-7638 ; 0000-0003-2050-2684 ; 0000-0001-6961-6047</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%2Fasia.202400749$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.202400749$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27911,27912,45561,45562</link.rule.ids></links><search><creatorcontrib>Peglow, Thiago J.</creatorcontrib><creatorcontrib>Thomaz, João Pedro S. S. C.</creatorcontrib><creatorcontrib>Nobre, Patrick C.</creatorcontrib><creatorcontrib>Scimmi, Cecilia</creatorcontrib><creatorcontrib>Santi, Claudio</creatorcontrib><creatorcontrib>Nascimento, Vanessa</creatorcontrib><title>Efficient Synthesis and Iodine‐Functionalization of Pyrazoles via KIO3/PhSeSePh System under Acidic Conditions</title><title>Chemistry, an Asian journal</title><description>This manuscript reports a novel method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and various hydrazines. In this approach, potassium iodate (KIO3) is used as the iodinating agent and (PhSe)2 is used as catalysts under acidic conditions. This protocol provides a convenient method for the efficient synthesis of 4‐iodo‐1‐aryl‐1H‐pyrazoles, valuable intermediates for several different coupling reactions.
We develop a new method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and hydrazines. In this approach, potassium iodate is used as the iodinating agent along with diphenyl diselenide under acidic conditions. The method is simple and efficient and allows the synthesis of 4‐iodopyrazoles and other iodinated heterocycles.</description><subject>catalysis</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Hydrazines</subject><subject>Iodination</subject><subject>Iodine</subject><subject>N-heterocycles</subject><subject>Pyrazole</subject><subject>selenium</subject><issn>1861-4728</issn><issn>1861-471X</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkM1Kw0AURoMoWKtb1wNu3LSdyfwly1BaDRZaiIK7ME5u6JR0EjOJkq58BJ_RJzGh0oWr-10494N7PO-W4CnB2J8pZ9TUxz7DWLLwzBuRQJAJk-T1_JT94NK7cm6HMfdxGIy8apHnRhuwDUo622zBGYeUzVBcZsbCz9f3srW6MaVVhTmoIaAyR5uuVoeyAIc-jEJP8ZrONtsEEths-x7XwB61NoMaRdpkRqN5aTMzHLtr7yJXhYObvzn2XpaL5_njZLV-iOfRalKRUIQTHuqAS0lBUkEDCRKY0L5UPJeK5CqTQmIm8FvOAxYQEAGTLNNEM06VZCqjY-_-2FvV5XsLrkn3xmkoCmWhbF1KcciJ9GkoevTuH7or27p_uKcI5VgKzv2eCo_UpymgS6va7FXdpQSng_10sJ-e7KdREkenjf4CJsx70Q</recordid><startdate>20241202</startdate><enddate>20241202</enddate><creator>Peglow, Thiago J.</creator><creator>Thomaz, João Pedro S. S. C.</creator><creator>Nobre, Patrick C.</creator><creator>Scimmi, Cecilia</creator><creator>Santi, Claudio</creator><creator>Nascimento, Vanessa</creator><general>Wiley Subscription Services, Inc</general><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7698-8970</orcidid><orcidid>https://orcid.org/0000-0001-9413-7638</orcidid><orcidid>https://orcid.org/0000-0003-2050-2684</orcidid><orcidid>https://orcid.org/0000-0001-6961-6047</orcidid></search><sort><creationdate>20241202</creationdate><title>Efficient Synthesis and Iodine‐Functionalization of Pyrazoles via KIO3/PhSeSePh System under Acidic Conditions</title><author>Peglow, Thiago J. ; Thomaz, João Pedro S. S. C. ; Nobre, Patrick C. ; Scimmi, Cecilia ; Santi, Claudio ; Nascimento, Vanessa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p1969-59c85773e736387e7e46c27a5f7a1fad7670460bf58481e68474dc1c453a74ad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>catalysis</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Hydrazines</topic><topic>Iodination</topic><topic>Iodine</topic><topic>N-heterocycles</topic><topic>Pyrazole</topic><topic>selenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peglow, Thiago J.</creatorcontrib><creatorcontrib>Thomaz, João Pedro S. S. C.</creatorcontrib><creatorcontrib>Nobre, Patrick C.</creatorcontrib><creatorcontrib>Scimmi, Cecilia</creatorcontrib><creatorcontrib>Santi, Claudio</creatorcontrib><creatorcontrib>Nascimento, Vanessa</creatorcontrib><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peglow, Thiago J.</au><au>Thomaz, João Pedro S. S. C.</au><au>Nobre, Patrick C.</au><au>Scimmi, Cecilia</au><au>Santi, Claudio</au><au>Nascimento, Vanessa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Synthesis and Iodine‐Functionalization of Pyrazoles via KIO3/PhSeSePh System under Acidic Conditions</atitle><jtitle>Chemistry, an Asian journal</jtitle><date>2024-12-02</date><risdate>2024</risdate><volume>19</volume><issue>23</issue><spage>e202400749</spage><epage>n/a</epage><pages>e202400749-n/a</pages><issn>1861-4728</issn><issn>1861-471X</issn><eissn>1861-471X</eissn><abstract>This manuscript reports a novel method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and various hydrazines. In this approach, potassium iodate (KIO3) is used as the iodinating agent and (PhSe)2 is used as catalysts under acidic conditions. This protocol provides a convenient method for the efficient synthesis of 4‐iodo‐1‐aryl‐1H‐pyrazoles, valuable intermediates for several different coupling reactions.
We develop a new method for the direct iodination of the C‐4 pyrazole ring generated in situ by the reaction of 1,1,3,3‐tetramethoxypropane and hydrazines. In this approach, potassium iodate is used as the iodinating agent along with diphenyl diselenide under acidic conditions. The method is simple and efficient and allows the synthesis of 4‐iodopyrazoles and other iodinated heterocycles.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/asia.202400749</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-7698-8970</orcidid><orcidid>https://orcid.org/0000-0001-9413-7638</orcidid><orcidid>https://orcid.org/0000-0003-2050-2684</orcidid><orcidid>https://orcid.org/0000-0001-6961-6047</orcidid></addata></record> |
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| issn | 1861-4728 1861-471X 1861-471X |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | catalysis Chemical reactions Chemical synthesis Hydrazines Iodination Iodine N-heterocycles Pyrazole selenium |
| title | Efficient Synthesis and Iodine‐Functionalization of Pyrazoles via KIO3/PhSeSePh System under Acidic Conditions |
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