Efficient Synthesis of New C-Functionalized Macrocyclic Polyamines
A powerful synthetic route for the preparation of new polyazamacrocycles, valuable precursors of bifunctional chelating agents with applications in nuclear medicine, is reported. The desired functional group was introduced onto the macrocycle backbone during the cyclization step, thus avoiding the t...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2010-03, Vol.2010 (9), p.1688-1693 |
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| container_issue | 9 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2010 |
| creator | Rousselin, Yoann Sok, Nicolas Boschetti, Frédéric Guilard, Roger Denat, Franck |
| description | A powerful synthetic route for the preparation of new polyazamacrocycles, valuable precursors of bifunctional chelating agents with applications in nuclear medicine, is reported. The desired functional group was introduced onto the macrocycle backbone during the cyclization step, thus avoiding the tedious preparation of a C‐functionalized synthon. The regioselective reaction of macrocycles bearing an aminomethyl pendant arm with aldehydes is also described.
We report a very convenient synthesis of cyclen and [13]aneN4 derivatives bearing an aminomethyl pendant group on a carbon atom. The cyclization step is performed by using chloroacetaldehyde and benzotriazole. The benzotriazole moiety is then replaced by a nitrile group, which is reduced to yield the target compounds. Such macrocycles can be further functionalized to give bifunctional chelatingagents. |
| doi_str_mv | 10.1002/ejoc.200901183 |
| format | Article |
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We report a very convenient synthesis of cyclen and [13]aneN4 derivatives bearing an aminomethyl pendant group on a carbon atom. The cyclization step is performed by using chloroacetaldehyde and benzotriazole. The benzotriazole moiety is then replaced by a nitrile group, which is reduced to yield the target compounds. Such macrocycles can be further functionalized to give bifunctional chelatingagents.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.200901183</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Amines ; Bifunctional chelating agents ; Chemical Sciences ; 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 ; Macrocycles ; N ligands ; Organic chemistry ; Preparations and properties</subject><ispartof>European Journal of Organic Chemistry, 2010-03, Vol.2010 (9), p.1688-1693</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3913-d3278ddf6f428159cef06928afa163bd6ff441ab7884706d7ae0f79279b49fb3</citedby><cites>FETCH-LOGICAL-c3913-d3278ddf6f428159cef06928afa163bd6ff441ab7884706d7ae0f79279b49fb3</cites><orcidid>0000-0002-3143-2135 ; 0000-0002-9652-4006 ; 0000-0002-6702-1303</orcidid></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.200901183$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.200901183$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,313,314,776,780,788,881,1411,27901,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22533316$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-00474575$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Rousselin, Yoann</creatorcontrib><creatorcontrib>Sok, Nicolas</creatorcontrib><creatorcontrib>Boschetti, Frédéric</creatorcontrib><creatorcontrib>Guilard, Roger</creatorcontrib><creatorcontrib>Denat, Franck</creatorcontrib><title>Efficient Synthesis of New C-Functionalized Macrocyclic Polyamines</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>A powerful synthetic route for the preparation of new polyazamacrocycles, valuable precursors of bifunctional chelating agents with applications in nuclear medicine, is reported. The desired functional group was introduced onto the macrocycle backbone during the cyclization step, thus avoiding the tedious preparation of a C‐functionalized synthon. The regioselective reaction of macrocycles bearing an aminomethyl pendant arm with aldehydes is also described.
We report a very convenient synthesis of cyclen and [13]aneN4 derivatives bearing an aminomethyl pendant group on a carbon atom. The cyclization step is performed by using chloroacetaldehyde and benzotriazole. The benzotriazole moiety is then replaced by a nitrile group, which is reduced to yield the target compounds. Such macrocycles can be further functionalized to give bifunctional chelatingagents.</description><subject>Amines</subject><subject>Bifunctional chelating agents</subject><subject>Chemical Sciences</subject><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>Macrocycles</subject><subject>N ligands</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkDtPwzAUhS0EEqWwMmdhYEjxK3E8lqgPUF8qlWCzHMdWXdKkigMl_HpSBUVsTPfq6nznHh0AbhEcIAjxg94VaoAh5BChiJyBHoKc-zDk8LzZKaE-4uTtElw5t4ONLAxRDzyOjLHK6rzyXuq82mpnnVcYb6GPXuyPP3JV2SKXmf3WqTeXqixUrTKrvFWR1XJvc-2uwYWRmdM3v7MPNuPRJp76s-XkKR7OfEU4In5KMIvS1ISG4ggFXGnTZMORNBKFJElDYyhFMmFRRBkMUyY1NIxjxhPKTUL64L613cpMHEq7l2UtCmnFdDgTpxuElNGABZ-o0Q5abZPXuVKbDkBQnMoSp7JEV1YD3LXAQTolM1PKXFnXURgHhJAmZh_wVne0ma7_cRWj52X894ffstZV-qtjZfkuQkZYIF4XE7HAY7Rez-diRX4AiWiJeQ</recordid><startdate>201003</startdate><enddate>201003</enddate><creator>Rousselin, Yoann</creator><creator>Sok, Nicolas</creator><creator>Boschetti, Frédéric</creator><creator>Guilard, Roger</creator><creator>Denat, Franck</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-3143-2135</orcidid><orcidid>https://orcid.org/0000-0002-9652-4006</orcidid><orcidid>https://orcid.org/0000-0002-6702-1303</orcidid></search><sort><creationdate>201003</creationdate><title>Efficient Synthesis of New C-Functionalized Macrocyclic Polyamines</title><author>Rousselin, Yoann ; Sok, Nicolas ; Boschetti, Frédéric ; Guilard, Roger ; Denat, Franck</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3913-d3278ddf6f428159cef06928afa163bd6ff441ab7884706d7ae0f79279b49fb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Amines</topic><topic>Bifunctional chelating agents</topic><topic>Chemical Sciences</topic><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>Macrocycles</topic><topic>N ligands</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rousselin, Yoann</creatorcontrib><creatorcontrib>Sok, Nicolas</creatorcontrib><creatorcontrib>Boschetti, Frédéric</creatorcontrib><creatorcontrib>Guilard, Roger</creatorcontrib><creatorcontrib>Denat, Franck</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rousselin, Yoann</au><au>Sok, Nicolas</au><au>Boschetti, Frédéric</au><au>Guilard, Roger</au><au>Denat, Franck</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Synthesis of New C-Functionalized Macrocyclic Polyamines</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2010-03</date><risdate>2010</risdate><volume>2010</volume><issue>9</issue><spage>1688</spage><epage>1693</epage><pages>1688-1693</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A powerful synthetic route for the preparation of new polyazamacrocycles, valuable precursors of bifunctional chelating agents with applications in nuclear medicine, is reported. The desired functional group was introduced onto the macrocycle backbone during the cyclization step, thus avoiding the tedious preparation of a C‐functionalized synthon. The regioselective reaction of macrocycles bearing an aminomethyl pendant arm with aldehydes is also described.
We report a very convenient synthesis of cyclen and [13]aneN4 derivatives bearing an aminomethyl pendant group on a carbon atom. The cyclization step is performed by using chloroacetaldehyde and benzotriazole. The benzotriazole moiety is then replaced by a nitrile group, which is reduced to yield the target compounds. Such macrocycles can be further functionalized to give bifunctional chelatingagents.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.200901183</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-3143-2135</orcidid><orcidid>https://orcid.org/0000-0002-9652-4006</orcidid><orcidid>https://orcid.org/0000-0002-6702-1303</orcidid></addata></record> |
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| ispartof | European Journal of Organic Chemistry, 2010-03, Vol.2010 (9), p.1688-1693 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley-Blackwell subscription journals |
| subjects | Amines Bifunctional chelating agents Chemical Sciences 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 Macrocycles N ligands Organic chemistry Preparations and properties |
| title | Efficient Synthesis of New C-Functionalized Macrocyclic Polyamines |
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