Studies on pyridazine azide cyclisation reactions

Studies on pyridazine azide cyclisation reactions

Reaction of sodium azide with 4-methyl-3,5,6-tribromopyridazine results in the formation of 3,5,6-triazide intermediate which could cyclise to give two possible bicyclic products while ab initio calculations show that the formation of a tricyclic compound is extremely energetically unfavourable. How...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic & biomolecular chemistry 2004-06, Vol.2 (12), p.1782-1788
Hauptverfasser: Allan, Robin D, Greenwood, Jeremy R, Hambley, Trevor W, Hanrahan, Jane R, Hibbs, David E, Itani, Samia, Tran, Hue W, Turner, Peter
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1788
container_issue 12
container_start_page 1782
container_title Organic & biomolecular chemistry
container_volume 2
creator Allan, Robin D
Greenwood, Jeremy R
Hambley, Trevor W
Hanrahan, Jane R
Hibbs, David E
Itani, Samia
Tran, Hue W
Turner, Peter
description Reaction of sodium azide with 4-methyl-3,5,6-tribromopyridazine results in the formation of 3,5,6-triazide intermediate which could cyclise to give two possible bicyclic products while ab initio calculations show that the formation of a tricyclic compound is extremely energetically unfavourable. However, experimentally, only one major product is isolated. The structure of this unstable product has been conclusively established by X-ray crystallography as 3,5-diazido-4-methyl[1,5-b]tetrazolopyridazine confirming theoretical predictions.
doi_str_mv 10.1039/b316190k
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_72008591</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>72008591</sourcerecordid><originalsourceid>FETCH-LOGICAL-c299t-bff18bd3b5e17e7cbbaf6029fb084999976c226dfd3666049dd645ca6521ce3f3</originalsourceid><addsrcrecordid>eNpFkE1LAzEQhoMotlbBXyB7Ei-rM8lusjlKqR9Q8KCel3xCdD9qsnuov94trTqHmRfm4T08hFwi3CIweacZcpTweUTmWAiRQ8nk8V-mMCNnKX0AoBS8OCUzLLGqoBBzgq_DaINLWd9lm20MVn2HzmXTti4zW9OEpIYwPaNTZhfSOTnxqknu4nAX5P1h9bZ8ytcvj8_L-3VuqJRDrr3HSlumS4fCCaO18hyo9BqqQk4juKGUW28Z5xwKaS0vSqN4SdE45tmCXO97N7H_Gl0a6jYk45pGda4fUy0oQFVKnMCbPWhin1J0vt7E0Kq4rRHqnZ76V8-EXh06R906-w8efLAfwYtffg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>72008591</pqid></control><display><type>article</type><title>Studies on pyridazine azide cyclisation reactions</title><source>Royal Society of Chemistry Journals Archive (1841-2007)</source><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Allan, Robin D ; Greenwood, Jeremy R ; Hambley, Trevor W ; Hanrahan, Jane R ; Hibbs, David E ; Itani, Samia ; Tran, Hue W ; Turner, Peter</creator><creatorcontrib>Allan, Robin D ; Greenwood, Jeremy R ; Hambley, Trevor W ; Hanrahan, Jane R ; Hibbs, David E ; Itani, Samia ; Tran, Hue W ; Turner, Peter</creatorcontrib><description>Reaction of sodium azide with 4-methyl-3,5,6-tribromopyridazine results in the formation of 3,5,6-triazide intermediate which could cyclise to give two possible bicyclic products while ab initio calculations show that the formation of a tricyclic compound is extremely energetically unfavourable. However, experimentally, only one major product is isolated. The structure of this unstable product has been conclusively established by X-ray crystallography as 3,5-diazido-4-methyl[1,5-b]tetrazolopyridazine confirming theoretical predictions.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b316190k</identifier><identifier>PMID: 15188047</identifier><language>eng</language><publisher>England</publisher><ispartof>Organic &amp; biomolecular chemistry, 2004-06, Vol.2 (12), p.1782-1788</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c299t-bff18bd3b5e17e7cbbaf6029fb084999976c226dfd3666049dd645ca6521ce3f3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,2817,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15188047$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Allan, Robin D</creatorcontrib><creatorcontrib>Greenwood, Jeremy R</creatorcontrib><creatorcontrib>Hambley, Trevor W</creatorcontrib><creatorcontrib>Hanrahan, Jane R</creatorcontrib><creatorcontrib>Hibbs, David E</creatorcontrib><creatorcontrib>Itani, Samia</creatorcontrib><creatorcontrib>Tran, Hue W</creatorcontrib><creatorcontrib>Turner, Peter</creatorcontrib><title>Studies on pyridazine azide cyclisation reactions</title><title>Organic &amp; biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Reaction of sodium azide with 4-methyl-3,5,6-tribromopyridazine results in the formation of 3,5,6-triazide intermediate which could cyclise to give two possible bicyclic products while ab initio calculations show that the formation of a tricyclic compound is extremely energetically unfavourable. However, experimentally, only one major product is isolated. The structure of this unstable product has been conclusively established by X-ray crystallography as 3,5-diazido-4-methyl[1,5-b]tetrazolopyridazine confirming theoretical predictions.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNpFkE1LAzEQhoMotlbBXyB7Ei-rM8lusjlKqR9Q8KCel3xCdD9qsnuov94trTqHmRfm4T08hFwi3CIweacZcpTweUTmWAiRQ8nk8V-mMCNnKX0AoBS8OCUzLLGqoBBzgq_DaINLWd9lm20MVn2HzmXTti4zW9OEpIYwPaNTZhfSOTnxqknu4nAX5P1h9bZ8ytcvj8_L-3VuqJRDrr3HSlumS4fCCaO18hyo9BqqQk4juKGUW28Z5xwKaS0vSqN4SdE45tmCXO97N7H_Gl0a6jYk45pGda4fUy0oQFVKnMCbPWhin1J0vt7E0Kq4rRHqnZ76V8-EXh06R906-w8efLAfwYtffg</recordid><startdate>20040621</startdate><enddate>20040621</enddate><creator>Allan, Robin D</creator><creator>Greenwood, Jeremy R</creator><creator>Hambley, Trevor W</creator><creator>Hanrahan, Jane R</creator><creator>Hibbs, David E</creator><creator>Itani, Samia</creator><creator>Tran, Hue W</creator><creator>Turner, Peter</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040621</creationdate><title>Studies on pyridazine azide cyclisation reactions</title><author>Allan, Robin D ; Greenwood, Jeremy R ; Hambley, Trevor W ; Hanrahan, Jane R ; Hibbs, David E ; Itani, Samia ; Tran, Hue W ; Turner, Peter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c299t-bff18bd3b5e17e7cbbaf6029fb084999976c226dfd3666049dd645ca6521ce3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Allan, Robin D</creatorcontrib><creatorcontrib>Greenwood, Jeremy R</creatorcontrib><creatorcontrib>Hambley, Trevor W</creatorcontrib><creatorcontrib>Hanrahan, Jane R</creatorcontrib><creatorcontrib>Hibbs, David E</creatorcontrib><creatorcontrib>Itani, Samia</creatorcontrib><creatorcontrib>Tran, Hue W</creatorcontrib><creatorcontrib>Turner, Peter</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic &amp; biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Allan, Robin D</au><au>Greenwood, Jeremy R</au><au>Hambley, Trevor W</au><au>Hanrahan, Jane R</au><au>Hibbs, David E</au><au>Itani, Samia</au><au>Tran, Hue W</au><au>Turner, Peter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on pyridazine azide cyclisation reactions</atitle><jtitle>Organic &amp; biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2004-06-21</date><risdate>2004</risdate><volume>2</volume><issue>12</issue><spage>1782</spage><epage>1788</epage><pages>1782-1788</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Reaction of sodium azide with 4-methyl-3,5,6-tribromopyridazine results in the formation of 3,5,6-triazide intermediate which could cyclise to give two possible bicyclic products while ab initio calculations show that the formation of a tricyclic compound is extremely energetically unfavourable. However, experimentally, only one major product is isolated. The structure of this unstable product has been conclusively established by X-ray crystallography as 3,5-diazido-4-methyl[1,5-b]tetrazolopyridazine confirming theoretical predictions.</abstract><cop>England</cop><pmid>15188047</pmid><doi>10.1039/b316190k</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof Organic & biomolecular chemistry, 2004-06, Vol.2 (12), p.1782-1788
issn 1477-0520
1477-0539
language eng
recordid cdi_proquest_miscellaneous_72008591
source Royal Society of Chemistry Journals Archive (1841-2007); Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
title Studies on pyridazine azide cyclisation reactions
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T00%3A22%3A22IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Studies%20on%20pyridazine%20azide%20cyclisation%20reactions&rft.jtitle=Organic%20&%20biomolecular%20chemistry&rft.au=Allan,%20Robin%20D&rft.date=2004-06-21&rft.volume=2&rft.issue=12&rft.spage=1782&rft.epage=1788&rft.pages=1782-1788&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/b316190k&rft_dat=%3Cproquest_cross%3E72008591%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=72008591&rft_id=info:pmid/15188047&rfr_iscdi=true