Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence

The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2013-07, Vol.15 (14), p.3798-3801
Main Authors: Trita, Andrada Stefania, Roisnel, Thierry, Mongin, Florence, Chevallier, Floris
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Chemical Sciences
Cyclization
Hydrogen Bonding
Hydrogenation
Macrocyclic Compounds - chemistry
Molecular Structure
Other
Pyridines - chemistry
Resorcinols - chemistry
Ruthenium - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763
cites cdi_FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763
container_end_page 3801
container_issue 14
container_start_page 3798
container_title Organic letters
container_volume 15
creator Trita, Andrada Stefania
Roisnel, Thierry
Mongin, Florence
Chevallier, Floris
description The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions employing a single ruthenium–alkylidene precatalyst open access to macrocyclic molecules.
doi_str_mv 10.1021/ol401803t
format article
fullrecord <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_01069852v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1434743292</sourcerecordid><originalsourceid>FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763</originalsourceid><addsrcrecordid>eNptkMtOwkAUQCdGI_hY-AOmGxNdVObRpzskKiYQFrIfb6e3tKTtYKc1wa93SAE3rubm5uTkziHkhtFHRjkb6dKjLKKiPSFD5nPhhtTnp8c5oANyYcyaUmY38TkZcBHxOKDxkHxOt2mjV1g7z7pOnSVWmxJaTB32xJw5qEarrSqLH2gLXTtt3uhulTtQO4sSs6J25thCm6MpzOhg6tEP_OqwVnhFzjIoDV7v30uyfH1ZTqbubPH2PhnPXBBe3LpebG_zQqApjxIacsWAI6LnMxHTJE1UwpTiKAAwA_s7lfihEF5IAVMIA3FJHnptDqXcNEUFzVZqKOR0PJO7HWU0iCOffzPL3vfsptH2SNPKqjAKyxJq1J2RzLNiT_CY_2ltCGMazI5uRuWuvTy2t-ztXtslFaZH8hDbAnc9AMrIte6a2gb5R_QLJriKrQ</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1434743292</pqid></control><display><type>article</type><title>Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Trita, Andrada Stefania ; Roisnel, Thierry ; Mongin, Florence ; Chevallier, Floris</creator><creatorcontrib>Trita, Andrada Stefania ; Roisnel, Thierry ; Mongin, Florence ; Chevallier, Floris</creatorcontrib><description>The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions employing a single ruthenium–alkylidene precatalyst open access to macrocyclic molecules.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol401803t</identifier><identifier>PMID: 23829609</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemistry ; Catalysis ; Chemical Sciences ; Cyclization ; Hydrogen Bonding ; Hydrogenation ; Macrocyclic Compounds - chemistry ; Molecular Structure ; Other ; Pyridines - chemistry ; Resorcinols - chemistry ; Ruthenium - chemistry</subject><ispartof>Organic letters, 2013-07, Vol.15 (14), p.3798-3801</ispartof><rights>Copyright © 2013 American Chemical Society</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763</citedby><cites>FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763</cites><orcidid>0000-0002-6088-4472 ; 0000-0003-3693-8861 ; 0000-0002-7482-9351</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23829609$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://hal.science/hal-01069852$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Trita, Andrada Stefania</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Mongin, Florence</creatorcontrib><creatorcontrib>Chevallier, Floris</creatorcontrib><title>Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions employing a single ruthenium–alkylidene precatalyst open access to macrocyclic molecules.</description><subject>Alkenes - chemistry</subject><subject>Catalysis</subject><subject>Chemical Sciences</subject><subject>Cyclization</subject><subject>Hydrogen Bonding</subject><subject>Hydrogenation</subject><subject>Macrocyclic Compounds - chemistry</subject><subject>Molecular Structure</subject><subject>Other</subject><subject>Pyridines - chemistry</subject><subject>Resorcinols - chemistry</subject><subject>Ruthenium - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkMtOwkAUQCdGI_hY-AOmGxNdVObRpzskKiYQFrIfb6e3tKTtYKc1wa93SAE3rubm5uTkziHkhtFHRjkb6dKjLKKiPSFD5nPhhtTnp8c5oANyYcyaUmY38TkZcBHxOKDxkHxOt2mjV1g7z7pOnSVWmxJaTB32xJw5qEarrSqLH2gLXTtt3uhulTtQO4sSs6J25thCm6MpzOhg6tEP_OqwVnhFzjIoDV7v30uyfH1ZTqbubPH2PhnPXBBe3LpebG_zQqApjxIacsWAI6LnMxHTJE1UwpTiKAAwA_s7lfihEF5IAVMIA3FJHnptDqXcNEUFzVZqKOR0PJO7HWU0iCOffzPL3vfsptH2SNPKqjAKyxJq1J2RzLNiT_CY_2ltCGMazI5uRuWuvTy2t-ztXtslFaZH8hDbAnc9AMrIte6a2gb5R_QLJriKrQ</recordid><startdate>20130719</startdate><enddate>20130719</enddate><creator>Trita, Andrada Stefania</creator><creator>Roisnel, Thierry</creator><creator>Mongin, Florence</creator><creator>Chevallier, Floris</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0003-3693-8861</orcidid><orcidid>https://orcid.org/0000-0002-7482-9351</orcidid></search><sort><creationdate>20130719</creationdate><title>Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence</title><author>Trita, Andrada Stefania ; Roisnel, Thierry ; Mongin, Florence ; Chevallier, Floris</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkenes - chemistry</topic><topic>Catalysis</topic><topic>Chemical Sciences</topic><topic>Cyclization</topic><topic>Hydrogen Bonding</topic><topic>Hydrogenation</topic><topic>Macrocyclic Compounds - chemistry</topic><topic>Molecular Structure</topic><topic>Other</topic><topic>Pyridines - chemistry</topic><topic>Resorcinols - chemistry</topic><topic>Ruthenium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trita, Andrada Stefania</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Mongin, Florence</creatorcontrib><creatorcontrib>Chevallier, Floris</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Trita, Andrada Stefania</au><au>Roisnel, Thierry</au><au>Mongin, Florence</au><au>Chevallier, Floris</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-07-19</date><risdate>2013</risdate><volume>15</volume><issue>14</issue><spage>3798</spage><epage>3801</epage><pages>3798-3801</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The construction of pyridine-containing macrocyclic architectures using a nonmetallic template is described. 4,6-Dichlororesorcinol was used as an exotemplate to self-organize two aza-heterocyclic units by OH···N hydrogen bonds. Subsequent sequential double olefin metathesis/hydrogenation reactions employing a single ruthenium–alkylidene precatalyst open access to macrocyclic molecules.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23829609</pmid><doi>10.1021/ol401803t</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0003-3693-8861</orcidid><orcidid>https://orcid.org/0000-0002-7482-9351</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2013-07, Vol.15 (14), p.3798-3801
issn 1523-7060
1523-7052
language eng
recordid cdi_hal_primary_oai_HAL_hal_01069852v1
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alkenes - chemistry
Catalysis
Chemical Sciences
Cyclization
Hydrogen Bonding
Hydrogenation
Macrocyclic Compounds - chemistry
Molecular Structure
Other
Pyridines - chemistry
Resorcinols - chemistry
Ruthenium - chemistry
title Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin Metathesis/Hydrogenation Sequence
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T14%3A52%3A29IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Hydrogen%20Bond%20Templated%201:1%20Macrocyclization%20through%20an%20Olefin%20Metathesis/Hydrogenation%20Sequence&rft.jtitle=Organic%20letters&rft.au=Trita,%20Andrada%20Stefania&rft.date=2013-07-19&rft.volume=15&rft.issue=14&rft.spage=3798&rft.epage=3801&rft.pages=3798-3801&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol401803t&rft_dat=%3Cproquest_hal_p%3E1434743292%3C/proquest_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a349t-4911547a0d28b072c1a2eee451390bdbcb1cc2e3aaefa052cb5733470aeda763%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1434743292&rft_id=info:pmid/23829609&rfr_iscdi=true