Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo-Condensed 1,3-Oxazines
Reaction of phenylpropynehydrazide with dimethylmalonyl chloride furnished the corresponding 4,4‐dimethyl‐1‐(3‐phenylprop‐2‐ynoyl)pyrazolidine‐3,5‐dione, which upon thermolysis underwent a 6‐endo‐dig cyclization to a pyrazolo[5,1‐b][1,3]oxazine. The corresponding reaction of arylpropynehydrazides wi...
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| Veröffentlicht in: | European journal of organic chemistry 2012-06, Vol.2012 (17), p.3219-3222 |
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| container_issue | 17 |
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| container_title | European journal of organic chemistry |
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| creator | Petina, Olga A. Yakovlev, Igor P. Geffken, Detlef |
| description | Reaction of phenylpropynehydrazide with dimethylmalonyl chloride furnished the corresponding 4,4‐dimethyl‐1‐(3‐phenylprop‐2‐ynoyl)pyrazolidine‐3,5‐dione, which upon thermolysis underwent a 6‐endo‐dig cyclization to a pyrazolo[5,1‐b][1,3]oxazine. The corresponding reaction of arylpropynehydrazides with monosubstituted malonyl chlorides furnished pyrazolo[5,1‐b][1,3]oxazine‐7‐ones via intermediates that could not be isolated.
The reaction of arylpropynehydrazides with monosubstituted malonyl chlorides leading to pyrazolo[5,1‐b][1,3]oxazines is reported. This method can also be extended to the synthesis of pyrazolidine‐3,5‐dione, which subsequently can be converted by thermolysis into a pyrazolo[5,1‐b][1,3]oxazine. |
| doi_str_mv | 10.1002/ejoc.201200267 |
| format | Article |
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The reaction of arylpropynehydrazides with monosubstituted malonyl chlorides leading to pyrazolo[5,1‐b][1,3]oxazines is reported. This method can also be extended to the synthesis of pyrazolidine‐3,5‐dione, which subsequently can be converted by thermolysis into a pyrazolo[5,1‐b][1,3]oxazine.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201200267</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Cyclization ; Cycloaddition ; Heterocycles ; Hydrazides ; Pyrazoles</subject><ispartof>European journal of organic chemistry, 2012-06, Vol.2012 (17), p.3219-3222</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3577-be98e1d0c448301c20e9a105b66b3ac5f8b276af7e9010aabe842d3cbc17c35a3</citedby><cites>FETCH-LOGICAL-c3577-be98e1d0c448301c20e9a105b66b3ac5f8b276af7e9010aabe842d3cbc17c35a3</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%2Fejoc.201200267$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201200267$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26042667$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Petina, Olga A.</creatorcontrib><creatorcontrib>Yakovlev, Igor P.</creatorcontrib><creatorcontrib>Geffken, Detlef</creatorcontrib><title>Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo-Condensed 1,3-Oxazines</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>Reaction of phenylpropynehydrazide with dimethylmalonyl chloride furnished the corresponding 4,4‐dimethyl‐1‐(3‐phenylprop‐2‐ynoyl)pyrazolidine‐3,5‐dione, which upon thermolysis underwent a 6‐endo‐dig cyclization to a pyrazolo[5,1‐b][1,3]oxazine. The corresponding reaction of arylpropynehydrazides with monosubstituted malonyl chlorides furnished pyrazolo[5,1‐b][1,3]oxazine‐7‐ones via intermediates that could not be isolated.
The reaction of arylpropynehydrazides with monosubstituted malonyl chlorides leading to pyrazolo[5,1‐b][1,3]oxazines is reported. This method can also be extended to the synthesis of pyrazolidine‐3,5‐dione, which subsequently can be converted by thermolysis into a pyrazolo[5,1‐b][1,3]oxazine.</description><subject>Cyclization</subject><subject>Cycloaddition</subject><subject>Heterocycles</subject><subject>Hydrazides</subject><subject>Pyrazoles</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAQxSMEEqWwMnthI-UcJ07NVqJSPgpFBUQ3y3EcNSXEwU7Vhr8el6KKjenu9N7vnfQ87xRDDwMEF2qhZS8AHLiDxnteBwNjPlAG-24PSehjRmaH3pG1CwBglOKO9zlVQjaFrizSORqYtqyNrttKzdvMiK8iUxatimaOnpepbYpm2agMPYhSV22JknmpzcZyiQZoqp2GGo2eWgfqUvuJrjJVWQfgc-JP1i6uUvbYO8hFadXJ7-x6r9fDl-TGH09Gt8lg7EsSxbGfKtZXOAMZhn0CWAagmMAQpZSmRMgo76dBTEUeKwYYhEhVPwwyIlOJY5cgSNfrbXOl0dYalfPaFB_CtBwD3xTGN4XxXWEOONsCtbBSlLkRlSzsjgoohAH98bGtb1WUqv0nlQ_vJsnfH_6WLWyj1jtWmHfu1Djib48jPsNR_Mjur_iYfAPGgo22</recordid><startdate>201206</startdate><enddate>201206</enddate><creator>Petina, Olga A.</creator><creator>Yakovlev, Igor P.</creator><creator>Geffken, Detlef</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201206</creationdate><title>Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo-Condensed 1,3-Oxazines</title><author>Petina, Olga A. ; Yakovlev, Igor P. ; Geffken, Detlef</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3577-be98e1d0c448301c20e9a105b66b3ac5f8b276af7e9010aabe842d3cbc17c35a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Cyclization</topic><topic>Cycloaddition</topic><topic>Heterocycles</topic><topic>Hydrazides</topic><topic>Pyrazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Petina, Olga A.</creatorcontrib><creatorcontrib>Yakovlev, Igor P.</creatorcontrib><creatorcontrib>Geffken, Detlef</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Petina, Olga A.</au><au>Yakovlev, Igor P.</au><au>Geffken, Detlef</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo-Condensed 1,3-Oxazines</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2012-06</date><risdate>2012</risdate><volume>2012</volume><issue>17</issue><spage>3219</spage><epage>3222</epage><pages>3219-3222</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Reaction of phenylpropynehydrazide with dimethylmalonyl chloride furnished the corresponding 4,4‐dimethyl‐1‐(3‐phenylprop‐2‐ynoyl)pyrazolidine‐3,5‐dione, which upon thermolysis underwent a 6‐endo‐dig cyclization to a pyrazolo[5,1‐b][1,3]oxazine. The corresponding reaction of arylpropynehydrazides with monosubstituted malonyl chlorides furnished pyrazolo[5,1‐b][1,3]oxazine‐7‐ones via intermediates that could not be isolated.
The reaction of arylpropynehydrazides with monosubstituted malonyl chlorides leading to pyrazolo[5,1‐b][1,3]oxazines is reported. This method can also be extended to the synthesis of pyrazolidine‐3,5‐dione, which subsequently can be converted by thermolysis into a pyrazolo[5,1‐b][1,3]oxazine.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201200267</doi><tpages>4</tpages></addata></record> |
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| source | Wiley Blackwell Single Titles |
| subjects | Cyclization Cycloaddition Heterocycles Hydrazides Pyrazoles |
| title | Reactions of Arylpropynehydrazides with Substituted Malonyl Chlorides: A Route to Pyrazolo-Condensed 1,3-Oxazines |
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