Unexpected ring closures leading to 2- N , N -dialkylaminoareno[1,3]tellurazoles
A novel synthetic method has been developed to prepare 2- N , N -areno[1,3]tellurazoles following a one step procedure from readily accessible precursors. Products were obtained in yields up to 78% by reacting bis(2-aminoaryl)ditellurides with dialkylformamides in the presence of phosphorous trichlo...
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Veröffentlicht in: | New journal of chemistry 2022-12, Vol.46 (47), p.22533-22538 |
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container_issue | 47 |
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container_title | New journal of chemistry |
container_volume | 46 |
creator | Pierre, Johan Hill, Zachary M. Fronczek, Frank R. Junk, Thomas |
description | A novel synthetic method has been developed to prepare 2-
N
,
N
-areno[1,3]tellurazoles following a one step procedure from readily accessible precursors. Products were obtained in yields up to 78% by reacting bis(2-aminoaryl)ditellurides with dialkylformamides in the presence of phosphorous trichloride or phosphorous oxychloride. An analogous approach furnished 2-(
N
,
N
-dimethylamino)naphtho[1,2-
d
][1,3]tellurazole from 3-chloronaphtho[2,1-
c
]-1,2,5-oxatellurazole. This method was found to be specific to the synthesis of 2-dialkylaminotellurazoles and does not proceed with sulfur or selenium congeners. A characterization of two selected samples by X-ray crystallography found a supramolecular wire motif resulting from intermolecular Te⋯N interactions for one of them. |
doi_str_mv | 10.1039/D2NJ03234A |
format | Article |
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N
,
N
-areno[1,3]tellurazoles following a one step procedure from readily accessible precursors. Products were obtained in yields up to 78% by reacting bis(2-aminoaryl)ditellurides with dialkylformamides in the presence of phosphorous trichloride or phosphorous oxychloride. An analogous approach furnished 2-(
N
,
N
-dimethylamino)naphtho[1,2-
d
][1,3]tellurazole from 3-chloronaphtho[2,1-
c
]-1,2,5-oxatellurazole. This method was found to be specific to the synthesis of 2-dialkylaminotellurazoles and does not proceed with sulfur or selenium congeners. A characterization of two selected samples by X-ray crystallography found a supramolecular wire motif resulting from intermolecular Te⋯N interactions for one of them.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/D2NJ03234A</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Chlorides ; Congeners ; Crystallography ; Selenium</subject><ispartof>New journal of chemistry, 2022-12, Vol.46 (47), p.22533-22538</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c259t-1bcd55aa2b84c02c3f9e671425afa838cee22f80b5f1a6a8d96fa8ea70208c5f3</citedby><cites>FETCH-LOGICAL-c259t-1bcd55aa2b84c02c3f9e671425afa838cee22f80b5f1a6a8d96fa8ea70208c5f3</cites><orcidid>0000-0003-0431-6582</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Pierre, Johan</creatorcontrib><creatorcontrib>Hill, Zachary M.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Junk, Thomas</creatorcontrib><title>Unexpected ring closures leading to 2- N , N -dialkylaminoareno[1,3]tellurazoles</title><title>New journal of chemistry</title><description>A novel synthetic method has been developed to prepare 2-
N
,
N
-areno[1,3]tellurazoles following a one step procedure from readily accessible precursors. Products were obtained in yields up to 78% by reacting bis(2-aminoaryl)ditellurides with dialkylformamides in the presence of phosphorous trichloride or phosphorous oxychloride. An analogous approach furnished 2-(
N
,
N
-dimethylamino)naphtho[1,2-
d
][1,3]tellurazole from 3-chloronaphtho[2,1-
c
]-1,2,5-oxatellurazole. This method was found to be specific to the synthesis of 2-dialkylaminotellurazoles and does not proceed with sulfur or selenium congeners. A characterization of two selected samples by X-ray crystallography found a supramolecular wire motif resulting from intermolecular Te⋯N interactions for one of them.</description><subject>Chlorides</subject><subject>Congeners</subject><subject>Crystallography</subject><subject>Selenium</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpFUEtLw0AYXETBWr34CwLepKv7TnIs9U2pHuxJJHzdfJHUbTbuJmD99aZU8DDMMAwzMIScc3bFmcyvb8TiiUkh1fSAjLg0Oc2F4YeD5kpRppU5JicxrhnjPDV8RF6WDX63aDssk1A3H4l1PvYBY-IQyp3R-UTQZJFMBtCyBve5dbCpGw8BG__GJ_K9Q-f6AD_eYTwlRxW4iGd_PCbLu9vX2QOdP98_zqZzaoXOO8pXttQaQKwyZZmwssrRpFwJDRVkMrOIQlQZW-mKg4GszM3gI6RMsMzqSo7Jxb63Df6rx9gVa9-HZpgsRKoMl1IZM6Qu9ykbfIwBq6IN9QbCtuCs2D1W_D8mfwEmql0R</recordid><startdate>20221205</startdate><enddate>20221205</enddate><creator>Pierre, Johan</creator><creator>Hill, Zachary M.</creator><creator>Fronczek, Frank R.</creator><creator>Junk, Thomas</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0003-0431-6582</orcidid></search><sort><creationdate>20221205</creationdate><title>Unexpected ring closures leading to 2- N , N -dialkylaminoareno[1,3]tellurazoles</title><author>Pierre, Johan ; Hill, Zachary M. ; Fronczek, Frank R. ; Junk, Thomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c259t-1bcd55aa2b84c02c3f9e671425afa838cee22f80b5f1a6a8d96fa8ea70208c5f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Chlorides</topic><topic>Congeners</topic><topic>Crystallography</topic><topic>Selenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pierre, Johan</creatorcontrib><creatorcontrib>Hill, Zachary M.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Junk, Thomas</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pierre, Johan</au><au>Hill, Zachary M.</au><au>Fronczek, Frank R.</au><au>Junk, Thomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Unexpected ring closures leading to 2- N , N -dialkylaminoareno[1,3]tellurazoles</atitle><jtitle>New journal of chemistry</jtitle><date>2022-12-05</date><risdate>2022</risdate><volume>46</volume><issue>47</issue><spage>22533</spage><epage>22538</epage><pages>22533-22538</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>A novel synthetic method has been developed to prepare 2-
N
,
N
-areno[1,3]tellurazoles following a one step procedure from readily accessible precursors. Products were obtained in yields up to 78% by reacting bis(2-aminoaryl)ditellurides with dialkylformamides in the presence of phosphorous trichloride or phosphorous oxychloride. An analogous approach furnished 2-(
N
,
N
-dimethylamino)naphtho[1,2-
d
][1,3]tellurazole from 3-chloronaphtho[2,1-
c
]-1,2,5-oxatellurazole. This method was found to be specific to the synthesis of 2-dialkylaminotellurazoles and does not proceed with sulfur or selenium congeners. A characterization of two selected samples by X-ray crystallography found a supramolecular wire motif resulting from intermolecular Te⋯N interactions for one of them.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D2NJ03234A</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-0431-6582</orcidid></addata></record> |
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language | eng |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Chlorides Congeners Crystallography Selenium |
title | Unexpected ring closures leading to 2- N , N -dialkylaminoareno[1,3]tellurazoles |
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