Regiospecific C-Acylation of Pyrroles and Indoles Using N-Acylbenzotriazoles
Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a−g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2-acylpyrroles 3a−g and 5a−g in good to excellent yields. 1...
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| Veröffentlicht in: | Journal of organic chemistry 2003-07, Vol.68 (14), p.5720-5723 |
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| container_title | Journal of organic chemistry |
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| creator | Katritzky, Alan R Suzuki, Kazuyuki Singh, Sandeep K He, Hai-Ying |
| description | Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a−g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2-acylpyrroles 3a−g and 5a−g in good to excellent yields. 1-Triisopropylsilylpyrrole (6) under the same conditions gave the respective 3-acylpyrroles 7a−g. Similarly, indole (9) and 1-methylindole (11) gave the corresponding 3-acylated derivatives 10a−g and 12a−g. These results demonstrate that N-acylbenzotriazoles such as 1c,f,g are mild, regioselective, and regiospecific C-acylating agents of particular utility when the corresponding acid chlorides are not readily available. |
| doi_str_mv | 10.1021/jo034187z |
| format | Article |
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Similarly, indole (9) and 1-methylindole (11) gave the corresponding 3-acylated derivatives 10a−g and 12a−g. These results demonstrate that N-acylbenzotriazoles such as 1c,f,g are mild, regioselective, and regiospecific C-acylating agents of particular utility when the corresponding acid chlorides are not readily available.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034187z</identifier><identifier>PMID: 12839468</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2003-07, Vol.68 (14), p.5720-5723</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-569f060e7c972f5194dd21765c5c253ce270ae6679718e7c9b5835aefc15967e3</citedby><cites>FETCH-LOGICAL-a445t-569f060e7c972f5194dd21765c5c253ce270ae6679718e7c9b5835aefc15967e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo034187z$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo034187z$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14951567$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12839468$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Katritzky, Alan R</creatorcontrib><creatorcontrib>Suzuki, Kazuyuki</creatorcontrib><creatorcontrib>Singh, Sandeep K</creatorcontrib><creatorcontrib>He, Hai-Ying</creatorcontrib><title>Regiospecific C-Acylation of Pyrroles and Indoles Using N-Acylbenzotriazoles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a−g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2-acylpyrroles 3a−g and 5a−g in good to excellent yields. 1-Triisopropylsilylpyrrole (6) under the same conditions gave the respective 3-acylpyrroles 7a−g. Similarly, indole (9) and 1-methylindole (11) gave the corresponding 3-acylated derivatives 10a−g and 12a−g. These results demonstrate that N-acylbenzotriazoles such as 1c,f,g are mild, regioselective, and regiospecific C-acylating agents of particular utility when the corresponding acid chlorides are not readily available.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><recordid>eNpt0ElLAzEYBuAgiq3LwT8gc1HwMJplvmTmKMWlUBdcsLeQZjIlOp3UZAq2v950wV7MJYH34cvHi9AJwZcEU3L16TDLSC4WO6hLgOKUFzjbRV2MKU0Z5ayDDkL4xPEAwD7qEJqzIuN5Fw1ezNi6MDXaVlYnvfRaz2vVWtckrkqe59672oRENWXSb8rV-z3YZpw8ruTINAvXeqsWy-gI7VWqDuZ4cx-i99ubt959Oni66_euB6nKMmhT4EWFOTZCF4JWQIqsLCkRHDRoCkwbKrAynItCkHypRpAzUKbSBAouDDtE5-u5U---Zya0cmKDNnWtGuNmQQoW_8kJjvBiDbV3IXhTyam3E-XnkmC5rE7-VRft6WbobDQx5VZuuorgbANU0KquvGq0DVuXFUCAi-jStbOhNT9_ufJfMqYC5Nvzq8TDj4chZEwOt3OVDnGfmW9id_8s-Atq6pB5</recordid><startdate>20030711</startdate><enddate>20030711</enddate><creator>Katritzky, Alan R</creator><creator>Suzuki, Kazuyuki</creator><creator>Singh, Sandeep K</creator><creator>He, Hai-Ying</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20030711</creationdate><title>Regiospecific C-Acylation of Pyrroles and Indoles Using N-Acylbenzotriazoles</title><author>Katritzky, Alan R ; Suzuki, Kazuyuki ; Singh, Sandeep K ; He, Hai-Ying</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-569f060e7c972f5194dd21765c5c253ce270ae6679718e7c9b5835aefc15967e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Katritzky, Alan R</creatorcontrib><creatorcontrib>Suzuki, Kazuyuki</creatorcontrib><creatorcontrib>Singh, Sandeep K</creatorcontrib><creatorcontrib>He, Hai-Ying</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Katritzky, Alan R</au><au>Suzuki, Kazuyuki</au><au>Singh, Sandeep K</au><au>He, Hai-Ying</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regiospecific C-Acylation of Pyrroles and Indoles Using N-Acylbenzotriazoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-07-11</date><risdate>2003</risdate><volume>68</volume><issue>14</issue><spage>5720</spage><epage>5723</epage><pages>5720-5723</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Reactions of pyrrole (2) or 1-methylpyrrole (4) with readily available N-acylbenzotriazoles 1a−g (RCOBt, where R = 4-tolyl, 4-nitrophenyl, 4-diethylaminophenyl, 2-furyl, 2-pyridyl, 2-indolyl, or 2-pyrrolyl) in the presence of TiCl4 produced 2-acylpyrroles 3a−g and 5a−g in good to excellent yields. 1-Triisopropylsilylpyrrole (6) under the same conditions gave the respective 3-acylpyrroles 7a−g. Similarly, indole (9) and 1-methylindole (11) gave the corresponding 3-acylated derivatives 10a−g and 12a−g. These results demonstrate that N-acylbenzotriazoles such as 1c,f,g are mild, regioselective, and regiospecific C-acylating agents of particular utility when the corresponding acid chlorides are not readily available.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12839468</pmid><doi>10.1021/jo034187z</doi><tpages>4</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Regiospecific C-Acylation of Pyrroles and Indoles Using N-Acylbenzotriazoles |
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