A reinvestigation of the reactions between diazomethane and 1-phenylurazole
Exhaustive methylation of 1‐phenylurazole (1), using ethereal diazomethane as the methylating agent, results in the formation of three products: 1‐phenyl‐3,5‐dimethoxy‐1,2,4‐triazole (2), 1‐phenyl‐3‐methoxy‐4‐methyl‐Δ2‐1,2,4‐triazolinev5‐one (3) and 1‐phenyl‐2,4‐dimethylurazole (4). Based on the amo...
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Veröffentlicht in: | Journal of physical organic chemistry 1993-11, Vol.6 (11), p.601-608 |
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description | Exhaustive methylation of 1‐phenylurazole (1), using ethereal diazomethane as the methylating agent, results in the formation of three products: 1‐phenyl‐3,5‐dimethoxy‐1,2,4‐triazole (2), 1‐phenyl‐3‐methoxy‐4‐methyl‐Δ2‐1,2,4‐triazolinev5‐one (3) and 1‐phenyl‐2,4‐dimethylurazole (4). Based on the amounts of 2–4 isolated, the overall yields in these reactions are typically >90%. When 1 and diazomethane were allowed to react in a fashion that resulted in the formation of monomethylated analogues of 1, 1‐phenyl‐3‐methoxy‐Δ2‐1,2,4‐triazoline‐5‐one (5) and 1‐phenylv2‐methylurazole (6) were formed. In separate experiments, the monomethylated species 5 and 6 were allowed to react with diazomethane in efforts to develop a sequence of reactions that reasonably accounts for the formation of 2–4. Whereas N‐ and O‐methylated products were obtained when 5 was treated with ethereal diazomethane, the reaction of 6 and diazomethane produced only the N‐alkylated product 1‐phenyl–2,4‐dimethylurazole (in quantitative yield). The outcomes of these experiments are consistent with a sequence of reactions in which the treatment of 1 with diazomethane results, initially, in the formation of the monomethylated species 5 and 6. In the presence of sufficient diazomethane, 5 and 6 then undergo further mothylation, forming the dimethylated species 2–4. |
doi_str_mv | 10.1002/poc.610061102 |
format | Article |
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J. ; Wang, L.-H.</creator><creatorcontrib>Bausch, M. J. ; Wang, L.-H.</creatorcontrib><description>Exhaustive methylation of 1‐phenylurazole (1), using ethereal diazomethane as the methylating agent, results in the formation of three products: 1‐phenyl‐3,5‐dimethoxy‐1,2,4‐triazole (2), 1‐phenyl‐3‐methoxy‐4‐methyl‐Δ2‐1,2,4‐triazolinev5‐one (3) and 1‐phenyl‐2,4‐dimethylurazole (4). Based on the amounts of 2–4 isolated, the overall yields in these reactions are typically >90%. When 1 and diazomethane were allowed to react in a fashion that resulted in the formation of monomethylated analogues of 1, 1‐phenyl‐3‐methoxy‐Δ2‐1,2,4‐triazoline‐5‐one (5) and 1‐phenylv2‐methylurazole (6) were formed. In separate experiments, the monomethylated species 5 and 6 were allowed to react with diazomethane in efforts to develop a sequence of reactions that reasonably accounts for the formation of 2–4. Whereas N‐ and O‐methylated products were obtained when 5 was treated with ethereal diazomethane, the reaction of 6 and diazomethane produced only the N‐alkylated product 1‐phenyl–2,4‐dimethylurazole (in quantitative yield). The outcomes of these experiments are consistent with a sequence of reactions in which the treatment of 1 with diazomethane results, initially, in the formation of the monomethylated species 5 and 6. In the presence of sufficient diazomethane, 5 and 6 then undergo further mothylation, forming the dimethylated species 2–4.</description><identifier>ISSN: 0894-3230</identifier><identifier>EISSN: 1099-1395</identifier><identifier>DOI: 10.1002/poc.610061102</identifier><identifier>CODEN: JPOCEE</identifier><language>eng</language><publisher>West Sussex: John Wiley & Sons, Ltd</publisher><subject>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 ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of physical organic chemistry, 1993-11, Vol.6 (11), p.601-608</ispartof><rights>Copyright © 1993 John Wiley & Sons, Ltd.</rights><rights>1994 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3082-b93dce2afba537af774aebfc54cff17e21d61d55f302838475e5178f2c7d29cb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpoc.610061102$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpoc.610061102$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27911,27912,45561,45562</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3859208$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Bausch, M. J.</creatorcontrib><creatorcontrib>Wang, L.-H.</creatorcontrib><title>A reinvestigation of the reactions between diazomethane and 1-phenylurazole</title><title>Journal of physical organic chemistry</title><addtitle>J. Phys. Org. Chem</addtitle><description>Exhaustive methylation of 1‐phenylurazole (1), using ethereal diazomethane as the methylating agent, results in the formation of three products: 1‐phenyl‐3,5‐dimethoxy‐1,2,4‐triazole (2), 1‐phenyl‐3‐methoxy‐4‐methyl‐Δ2‐1,2,4‐triazolinev5‐one (3) and 1‐phenyl‐2,4‐dimethylurazole (4). Based on the amounts of 2–4 isolated, the overall yields in these reactions are typically >90%. When 1 and diazomethane were allowed to react in a fashion that resulted in the formation of monomethylated analogues of 1, 1‐phenyl‐3‐methoxy‐Δ2‐1,2,4‐triazoline‐5‐one (5) and 1‐phenylv2‐methylurazole (6) were formed. In separate experiments, the monomethylated species 5 and 6 were allowed to react with diazomethane in efforts to develop a sequence of reactions that reasonably accounts for the formation of 2–4. Whereas N‐ and O‐methylated products were obtained when 5 was treated with ethereal diazomethane, the reaction of 6 and diazomethane produced only the N‐alkylated product 1‐phenyl–2,4‐dimethylurazole (in quantitative yield). The outcomes of these experiments are consistent with a sequence of reactions in which the treatment of 1 with diazomethane results, initially, in the formation of the monomethylated species 5 and 6. In the presence of sufficient diazomethane, 5 and 6 then undergo further mothylation, forming the dimethylated species 2–4.</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>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0894-3230</issn><issn>1099-1395</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><recordid>eNp9UDtPwzAQthBIlMLInoE1xY84jseqogVRtQiBYLMc50wNaRLZgRJ-PalaVUxM9_ged_oQuiR4RDCm101tRmnfpYRgeoQGBEsZEyb5MRrgTCYxowyforMQ3jHuMS4G6H4ceXDVF4TWvenW1VVU26hdQb_WZjuHKId2A1BFhdM_9Rrala4g0lURkbhZQdWVn74HSjhHJ1aXAS72dYiepzdPk9t4vpzdTcbz2DCc0TiXrDBAtc01Z0JbIRINuTU8MdYSAZQUKSk4twzTjGWJ4MCJyCw1oqDS5GyI4p2v8XUIHqxqvFtr3ymC1TYJ1SehDkn0_Ksdv9HB6NJ6XRkXDiKWcUlx1tPEjrZxJXT_e6qH5eTvgf1DLrTwfVBq_6FSwQRXL4uZepzKxaucSZWyX9iJfpQ</recordid><startdate>199311</startdate><enddate>199311</enddate><creator>Bausch, M. J.</creator><creator>Wang, L.-H.</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199311</creationdate><title>A reinvestigation of the reactions between diazomethane and 1-phenylurazole</title><author>Bausch, M. J. ; Wang, L.-H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3082-b93dce2afba537af774aebfc54cff17e21d61d55f302838475e5178f2c7d29cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</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>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bausch, M. J.</creatorcontrib><creatorcontrib>Wang, L.-H.</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Journal of physical organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bausch, M. J.</au><au>Wang, L.-H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A reinvestigation of the reactions between diazomethane and 1-phenylurazole</atitle><jtitle>Journal of physical organic chemistry</jtitle><addtitle>J. Phys. Org. Chem</addtitle><date>1993-11</date><risdate>1993</risdate><volume>6</volume><issue>11</issue><spage>601</spage><epage>608</epage><pages>601-608</pages><issn>0894-3230</issn><eissn>1099-1395</eissn><coden>JPOCEE</coden><abstract>Exhaustive methylation of 1‐phenylurazole (1), using ethereal diazomethane as the methylating agent, results in the formation of three products: 1‐phenyl‐3,5‐dimethoxy‐1,2,4‐triazole (2), 1‐phenyl‐3‐methoxy‐4‐methyl‐Δ2‐1,2,4‐triazolinev5‐one (3) and 1‐phenyl‐2,4‐dimethylurazole (4). Based on the amounts of 2–4 isolated, the overall yields in these reactions are typically >90%. When 1 and diazomethane were allowed to react in a fashion that resulted in the formation of monomethylated analogues of 1, 1‐phenyl‐3‐methoxy‐Δ2‐1,2,4‐triazoline‐5‐one (5) and 1‐phenylv2‐methylurazole (6) were formed. In separate experiments, the monomethylated species 5 and 6 were allowed to react with diazomethane in efforts to develop a sequence of reactions that reasonably accounts for the formation of 2–4. Whereas N‐ and O‐methylated products were obtained when 5 was treated with ethereal diazomethane, the reaction of 6 and diazomethane produced only the N‐alkylated product 1‐phenyl–2,4‐dimethylurazole (in quantitative yield). The outcomes of these experiments are consistent with a sequence of reactions in which the treatment of 1 with diazomethane results, initially, in the formation of the monomethylated species 5 and 6. In the presence of sufficient diazomethane, 5 and 6 then undergo further mothylation, forming the dimethylated species 2–4.</abstract><cop>West Sussex</cop><pub>John Wiley & Sons, Ltd</pub><doi>10.1002/poc.610061102</doi><tpages>8</tpages></addata></record> |
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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 Organic chemistry Preparations and properties |
title | A reinvestigation of the reactions between diazomethane and 1-phenylurazole |
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