A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis

Azo coupling of 1,3‐dicarbonyl compounds with tetrazolyl‐5‐diazonium chloride is used to develop a convenient one‐step procedure for the synthesis of 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7‐hydroxy‐7‐polyfluoroalkyl‐4,7‐dihydrotetrazolo[5,1‐c][1,2,4]tria...

Full description

Saved in:
Bibliographic Details
Published in:Journal of heterocyclic chemistry 2013-02, Vol.50 (S1), p.E80-E86
Main Authors: Shchegol'kov, Evgeny V., Ivanova, Anna E., Burgart, Yanina V., Saloutin, Viktor I.
Format: Article
Language:English
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-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823
cites cdi_FETCH-LOGICAL-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823
container_end_page E86
container_issue S1
container_start_page E80
container_title Journal of heterocyclic chemistry
container_volume 50
creator Shchegol'kov, Evgeny V.
Ivanova, Anna E.
Burgart, Yanina V.
Saloutin, Viktor I.
description Azo coupling of 1,3‐dicarbonyl compounds with tetrazolyl‐5‐diazonium chloride is used to develop a convenient one‐step procedure for the synthesis of 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7‐hydroxy‐7‐polyfluoroalkyl‐4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines undergo a ring‐chain isomerism resulting from the cleavage at the C7―N7a bond. A distinctive feature of nonfluorinated 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines is the possibility to dehydration, which is accompanied by an azide rearrangement due to the tetrazole ring cleavage with the formation of tetrazolo[1,5‐b][1,2,4]triazines.
doi_str_mv 10.1002/jhet.1068
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1350555137</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2969325011</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823</originalsourceid><addsrcrecordid>eNp1kF1PwjAUhhujiYhe-A-WeGWyST9W1l4iIkgQL8RIJKTpti4r4oZtUcevd2TEO6_OOTnPez5eAC4RvEEQ4s4qV67OuuwItBAPSUARJ8egVfdwgCien4Iza1d1iUgUtcC05_XL4ksVWhXO6202ppRJ7rnSC_0ouNN5lZrSKWfkrlyX3oL6KEiWC-RjP1w6o-VOF8p7rgqXK6vtOTjJ5Nqqi0Nsg5f7waw_CiZPw4d-bxIkhFAWcCg5S3gSS8IRl7GCkOAsTiXBFLOQhilWTGEJWRJlMOaKMpYSEsZJTNOQYdIGV83c-t7PrbJOrMqtKeqVAhEKKaX1ezV13VCJKa01KhMboz-kqQSCYm-X2Nsl9nbVbKdhv_VaVf-DYjwazA6KoFFo69TPn0Kad9GNSETF63QoGHp7RNH8VozJLzbveac</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1350555137</pqid></control><display><type>article</type><title>A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis</title><source>Wiley</source><creator>Shchegol'kov, Evgeny V. ; Ivanova, Anna E. ; Burgart, Yanina V. ; Saloutin, Viktor I.</creator><creatorcontrib>Shchegol'kov, Evgeny V. ; Ivanova, Anna E. ; Burgart, Yanina V. ; Saloutin, Viktor I.</creatorcontrib><description>Azo coupling of 1,3‐dicarbonyl compounds with tetrazolyl‐5‐diazonium chloride is used to develop a convenient one‐step procedure for the synthesis of 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7‐hydroxy‐7‐polyfluoroalkyl‐4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines undergo a ring‐chain isomerism resulting from the cleavage at the C7―N7a bond. A distinctive feature of nonfluorinated 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines is the possibility to dehydration, which is accompanied by an azide rearrangement due to the tetrazole ring cleavage with the formation of tetrazolo[1,5‐b][1,2,4]triazines.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.1068</identifier><language>eng</language><publisher>Hoboken: Blackwell Publishing Ltd</publisher><ispartof>Journal of heterocyclic chemistry, 2013-02, Vol.50 (S1), p.E80-E86</ispartof><rights>2013 HeteroCorporation</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823</citedby><cites>FETCH-LOGICAL-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Shchegol'kov, Evgeny V.</creatorcontrib><creatorcontrib>Ivanova, Anna E.</creatorcontrib><creatorcontrib>Burgart, Yanina V.</creatorcontrib><creatorcontrib>Saloutin, Viktor I.</creatorcontrib><title>A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis</title><title>Journal of heterocyclic chemistry</title><addtitle>J. Heterocyclic Chem</addtitle><description>Azo coupling of 1,3‐dicarbonyl compounds with tetrazolyl‐5‐diazonium chloride is used to develop a convenient one‐step procedure for the synthesis of 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7‐hydroxy‐7‐polyfluoroalkyl‐4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines undergo a ring‐chain isomerism resulting from the cleavage at the C7―N7a bond. A distinctive feature of nonfluorinated 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines is the possibility to dehydration, which is accompanied by an azide rearrangement due to the tetrazole ring cleavage with the formation of tetrazolo[1,5‐b][1,2,4]triazines.</description><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp1kF1PwjAUhhujiYhe-A-WeGWyST9W1l4iIkgQL8RIJKTpti4r4oZtUcevd2TEO6_OOTnPez5eAC4RvEEQ4s4qV67OuuwItBAPSUARJ8egVfdwgCien4Iza1d1iUgUtcC05_XL4ksVWhXO6202ppRJ7rnSC_0ouNN5lZrSKWfkrlyX3oL6KEiWC-RjP1w6o-VOF8p7rgqXK6vtOTjJ5Nqqi0Nsg5f7waw_CiZPw4d-bxIkhFAWcCg5S3gSS8IRl7GCkOAsTiXBFLOQhilWTGEJWRJlMOaKMpYSEsZJTNOQYdIGV83c-t7PrbJOrMqtKeqVAhEKKaX1ezV13VCJKa01KhMboz-kqQSCYm-X2Nsl9nbVbKdhv_VaVf-DYjwazA6KoFFo69TPn0Kad9GNSETF63QoGHp7RNH8VozJLzbveac</recordid><startdate>201302</startdate><enddate>201302</enddate><creator>Shchegol'kov, Evgeny V.</creator><creator>Ivanova, Anna E.</creator><creator>Burgart, Yanina V.</creator><creator>Saloutin, Viktor I.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201302</creationdate><title>A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis</title><author>Shchegol'kov, Evgeny V. ; Ivanova, Anna E. ; Burgart, Yanina V. ; Saloutin, Viktor I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shchegol'kov, Evgeny V.</creatorcontrib><creatorcontrib>Ivanova, Anna E.</creatorcontrib><creatorcontrib>Burgart, Yanina V.</creatorcontrib><creatorcontrib>Saloutin, Viktor I.</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shchegol'kov, Evgeny V.</au><au>Ivanova, Anna E.</au><au>Burgart, Yanina V.</au><au>Saloutin, Viktor I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><addtitle>J. Heterocyclic Chem</addtitle><date>2013-02</date><risdate>2013</risdate><volume>50</volume><issue>S1</issue><spage>E80</spage><epage>E86</epage><pages>E80-E86</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>Azo coupling of 1,3‐dicarbonyl compounds with tetrazolyl‐5‐diazonium chloride is used to develop a convenient one‐step procedure for the synthesis of 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines. In contrast to nonfluorinated analogs, 7‐hydroxy‐7‐polyfluoroalkyl‐4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines undergo a ring‐chain isomerism resulting from the cleavage at the C7―N7a bond. A distinctive feature of nonfluorinated 4,7‐dihydrotetrazolo[5,1‐c][1,2,4]triazines is the possibility to dehydration, which is accompanied by an azide rearrangement due to the tetrazole ring cleavage with the formation of tetrazolo[1,5‐b][1,2,4]triazines.</abstract><cop>Hoboken</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/jhet.1068</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-152X
ispartof Journal of heterocyclic chemistry, 2013-02, Vol.50 (S1), p.E80-E86
issn 0022-152X
1943-5193
language eng
recordid cdi_proquest_journals_1350555137
source Wiley
title A Convenient Approach to 4,7-Dihydrotetrazolo [5,1-c][1,2,4]triazine Synthesis
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T17%3A26%3A58IST&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=A%20Convenient%20Approach%20to%204,7-Dihydrotetrazolo%20%5B5,1-c%5D%5B1,2,4%5Dtriazine%20Synthesis&rft.jtitle=Journal%20of%20heterocyclic%20chemistry&rft.au=Shchegol'kov,%20Evgeny%20V.&rft.date=2013-02&rft.volume=50&rft.issue=S1&rft.spage=E80&rft.epage=E86&rft.pages=E80-E86&rft.issn=0022-152X&rft.eissn=1943-5193&rft_id=info:doi/10.1002/jhet.1068&rft_dat=%3Cproquest_cross%3E2969325011%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3358-90a98c9cba3919abe0032fbda32528454d2e8e2a08c7f0b9e588d334bcb5d4823%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1350555137&rft_id=info:pmid/&rfr_iscdi=true