Site Selectivity in the Synthesis of O-Methylated Hydroxamic Acids with Diazomethane
In this paper we report the results obtained by treating some selected hydroxamic acids with diazomethane in ethereal media. The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation p...
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| Veröffentlicht in: | Journal of organic chemistry 2001-04, Vol.66 (7), p.2246-2250 |
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| container_end_page | 2250 |
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| container_issue | 7 |
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| container_title | Journal of organic chemistry |
| container_volume | 66 |
| creator | Leggio, Antonella Liguori, Angelo Napoli, Anna Siciliano, Carlo Sindona, Giovanni |
| description | In this paper we report the results obtained by treating some selected hydroxamic acids with diazomethane in ethereal media. The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation processes of the generated anions. Product distributions clearly showed that a high site selectivity is expressed by the different deprotonated species in the alkylation processes. Under the adopted conditions, the prevalent site of methylation is in all the cases the oxygen of the hydroxamic acid. While in aliphatic hydroxamic acids only O-alkylation is observed, in the aromatic substrates, the NH group competes with the OH function as the nucleophilic site, although the OH reactivity still dominates. |
| doi_str_mv | 10.1021/jo0012391 |
| format | Article |
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The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation processes of the generated anions. Product distributions clearly showed that a high site selectivity is expressed by the different deprotonated species in the alkylation processes. Under the adopted conditions, the prevalent site of methylation is in all the cases the oxygen of the hydroxamic acid. While in aliphatic hydroxamic acids only O-alkylation is observed, in the aromatic substrates, the NH group competes with the OH function as the nucleophilic site, although the OH reactivity still dominates.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo0012391</identifier><identifier>PMID: 11281763</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Diazomethane - chemistry ; Hydroxamic Acids - chemical synthesis ; Methylation ; Substrate Specificity</subject><ispartof>Journal of organic chemistry, 2001-04, Vol.66 (7), p.2246-2250</ispartof><rights>Copyright © 2001 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a318t-c48095fadcbbf00862709843aadd8defee31d881ae645c5c06529265bf5a29183</citedby><cites>FETCH-LOGICAL-a318t-c48095fadcbbf00862709843aadd8defee31d881ae645c5c06529265bf5a29183</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/jo0012391$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo0012391$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11281763$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Leggio, Antonella</creatorcontrib><creatorcontrib>Liguori, Angelo</creatorcontrib><creatorcontrib>Napoli, Anna</creatorcontrib><creatorcontrib>Siciliano, Carlo</creatorcontrib><creatorcontrib>Sindona, Giovanni</creatorcontrib><title>Site Selectivity in the Synthesis of O-Methylated Hydroxamic Acids with Diazomethane</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>In this paper we report the results obtained by treating some selected hydroxamic acids with diazomethane in ethereal media. The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation processes of the generated anions. Product distributions clearly showed that a high site selectivity is expressed by the different deprotonated species in the alkylation processes. Under the adopted conditions, the prevalent site of methylation is in all the cases the oxygen of the hydroxamic acid. While in aliphatic hydroxamic acids only O-alkylation is observed, in the aromatic substrates, the NH group competes with the OH function as the nucleophilic site, although the OH reactivity still dominates.</description><subject>Diazomethane - chemistry</subject><subject>Hydroxamic Acids - chemical synthesis</subject><subject>Methylation</subject><subject>Substrate Specificity</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0D1PwzAQBmALgWgpDPwB5IWBIeCP2HHGUj6KaFWkFDFGju2oLk1TxS40_HqMUsGCl5N8j-50LwDnGF1jRPDNskYIE5riA9DHjKCIpyg-BH2ECIko4bQHTpxbovAYY8eghzEROOG0D-aZ9QZmZmWUtx_Wt9CuoV-Er3YdirMO1iWcRVPjF-1KeqPhuNVNvZOVVXCorHbw0_oFvLPyq66CkmtzCo5KuXLmbF8H4PXhfj4aR5PZ49NoOIkkxcJHKhYoZaXUqihKhAQnCUpFTKXUWmhTGkOxFgJLw2OmmEKckZRwVpRMkhQLOgBX3VzV1M41psw3ja1k0-YY5T_J5L_JBHvR2c22qIz-k_soAog6YJ03u9--bN5zntCE5fOXLM-mt5NR9sby5-AvOy-VC3u2zTqc-s_ib3E0eS8</recordid><startdate>20010406</startdate><enddate>20010406</enddate><creator>Leggio, Antonella</creator><creator>Liguori, Angelo</creator><creator>Napoli, Anna</creator><creator>Siciliano, Carlo</creator><creator>Sindona, Giovanni</creator><general>American Chemical Society</general><scope>BSCLL</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></search><sort><creationdate>20010406</creationdate><title>Site Selectivity in the Synthesis of O-Methylated Hydroxamic Acids with Diazomethane</title><author>Leggio, Antonella ; Liguori, Angelo ; Napoli, Anna ; Siciliano, Carlo ; Sindona, Giovanni</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a318t-c48095fadcbbf00862709843aadd8defee31d881ae645c5c06529265bf5a29183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Diazomethane - chemistry</topic><topic>Hydroxamic Acids - chemical synthesis</topic><topic>Methylation</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leggio, Antonella</creatorcontrib><creatorcontrib>Liguori, Angelo</creatorcontrib><creatorcontrib>Napoli, Anna</creatorcontrib><creatorcontrib>Siciliano, Carlo</creatorcontrib><creatorcontrib>Sindona, Giovanni</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Leggio, Antonella</au><au>Liguori, Angelo</au><au>Napoli, Anna</au><au>Siciliano, Carlo</au><au>Sindona, Giovanni</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site Selectivity in the Synthesis of O-Methylated Hydroxamic Acids with Diazomethane</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2001-04-06</date><risdate>2001</risdate><volume>66</volume><issue>7</issue><spage>2246</spage><epage>2250</epage><pages>2246-2250</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>In this paper we report the results obtained by treating some selected hydroxamic acids with diazomethane in ethereal media. The multitask reagent diazomethane was used either as a base to induce deprotonation of the chosen hydroxamic acids or as conjugated acid which undergoes one-pot methylation processes of the generated anions. Product distributions clearly showed that a high site selectivity is expressed by the different deprotonated species in the alkylation processes. Under the adopted conditions, the prevalent site of methylation is in all the cases the oxygen of the hydroxamic acid. While in aliphatic hydroxamic acids only O-alkylation is observed, in the aromatic substrates, the NH group competes with the OH function as the nucleophilic site, although the OH reactivity still dominates.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11281763</pmid><doi>10.1021/jo0012391</doi><tpages>5</tpages></addata></record> |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Diazomethane - chemistry Hydroxamic Acids - chemical synthesis Methylation Substrate Specificity |
| title | Site Selectivity in the Synthesis of O-Methylated Hydroxamic Acids with Diazomethane |
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