The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides

The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-10, Vol.56 (10), p.1341-1347
Main Authors: Dianova, Lidiya N., Beryozkina, Tetyana V., Filimonov, Valeriy O., Fan, Zhijin, Slepukhin, Pavel А., Bakulev, Vasiliy А.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites cdi_FETCH-LOGICAL-c242t-ab07eff0f06504978f1e64103cf9be2f6eec8fc2ce82da940f2466cf74ebb3153
container_end_page 1347
container_issue 10
container_start_page 1341
container_title Chemistry of heterocyclic compounds (New York, N.Y. 1965)
container_volume 56
creator Dianova, Lidiya N.
Beryozkina, Tetyana V.
Filimonov, Valeriy O.
Fan, Zhijin
Slepukhin, Pavel А.
Bakulev, Vasiliy А.
description The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed by the synthesis of the target products via the reaction of 5-arylamino-1,2,3-triazole-4-carbothioamides with sulfonyl and acyl chlorides.
doi_str_mv 10.1007/s10593-020-02820-3
format article
fullrecord <record><control><sourceid>crossref_sprin</sourceid><recordid>TN_cdi_crossref_primary_10_1007_s10593_020_02820_3</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1007_s10593_020_02820_3</sourcerecordid><originalsourceid>FETCH-LOGICAL-c242t-ab07eff0f06504978f1e64103cf9be2f6eec8fc2ce82da940f2466cf74ebb3153</originalsourceid><addsrcrecordid>eNp9kM1KAzEUhYMoWKsv4CoP0Nj8zO9S6i8Ibup6yGRu2pSZiSSpUJ_Mx_PWFnHlIrkJ95zD4SPkWvAbwXk5j4LntWJccjwV3uqETEReKlapXJ2SCee8ZkpIeU4uYtzgtxRVNiFfyzXQpMcOBnrnhuDTmgbQIehxBQOMieKOxm1v_bjrdXJ-nGtzfFEdUbxyPkIPJrkPoAOkte-o9YEmTI67EUd0kXpLc6YDOgc3eibZbybmS7bPZH8FYiZniqXg9KfvgWXM6NBiO-dx30G8JGdW9xGujnNK3h7ul4sn9vL6-Ly4fWFGZjIx3fISrOWWFznP6rKyAopMcGVs3YK0BYCprJEGKtnpOuNWZkVhbJlB2yqRqymRh1wTfIwBbPMe3IA9G8GbPfvmwL5B9s0P-0ahSR1MEcUIMjQbvw0j9vzP9Q1ZnoxI</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides</title><source>Springer Link</source><creator>Dianova, Lidiya N. ; Beryozkina, Tetyana V. ; Filimonov, Valeriy O. ; Fan, Zhijin ; Slepukhin, Pavel А. ; Bakulev, Vasiliy А.</creator><creatorcontrib>Dianova, Lidiya N. ; Beryozkina, Tetyana V. ; Filimonov, Valeriy O. ; Fan, Zhijin ; Slepukhin, Pavel А. ; Bakulev, Vasiliy А.</creatorcontrib><description>The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed by the synthesis of the target products via the reaction of 5-arylamino-1,2,3-triazole-4-carbothioamides with sulfonyl and acyl chlorides.</description><identifier>ISSN: 0009-3122</identifier><identifier>EISSN: 1573-8353</identifier><identifier>DOI: 10.1007/s10593-020-02820-3</identifier><language>eng</language><publisher>New York: Springer US</publisher><subject>Chemistry ; Chemistry and Materials Science ; Organic Chemistry ; Pharmacy</subject><ispartof>Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2020-10, Vol.56 (10), p.1341-1347</ispartof><rights>Springer Science+Business Media, LLC, part of Springer Nature 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c242t-ab07eff0f06504978f1e64103cf9be2f6eec8fc2ce82da940f2466cf74ebb3153</cites></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>Dianova, Lidiya N.</creatorcontrib><creatorcontrib>Beryozkina, Tetyana V.</creatorcontrib><creatorcontrib>Filimonov, Valeriy O.</creatorcontrib><creatorcontrib>Fan, Zhijin</creatorcontrib><creatorcontrib>Slepukhin, Pavel А.</creatorcontrib><creatorcontrib>Bakulev, Vasiliy А.</creatorcontrib><title>The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides</title><title>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</title><addtitle>Chem Heterocycl Comp</addtitle><description>The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed by the synthesis of the target products via the reaction of 5-arylamino-1,2,3-triazole-4-carbothioamides with sulfonyl and acyl chlorides.</description><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kM1KAzEUhYMoWKsv4CoP0Nj8zO9S6i8Ibup6yGRu2pSZiSSpUJ_Mx_PWFnHlIrkJ95zD4SPkWvAbwXk5j4LntWJccjwV3uqETEReKlapXJ2SCee8ZkpIeU4uYtzgtxRVNiFfyzXQpMcOBnrnhuDTmgbQIehxBQOMieKOxm1v_bjrdXJ-nGtzfFEdUbxyPkIPJrkPoAOkte-o9YEmTI67EUd0kXpLc6YDOgc3eibZbybmS7bPZH8FYiZniqXg9KfvgWXM6NBiO-dx30G8JGdW9xGujnNK3h7ul4sn9vL6-Ly4fWFGZjIx3fISrOWWFznP6rKyAopMcGVs3YK0BYCprJEGKtnpOuNWZkVhbJlB2yqRqymRh1wTfIwBbPMe3IA9G8GbPfvmwL5B9s0P-0ahSR1MEcUIMjQbvw0j9vzP9Q1ZnoxI</recordid><startdate>20201001</startdate><enddate>20201001</enddate><creator>Dianova, Lidiya N.</creator><creator>Beryozkina, Tetyana V.</creator><creator>Filimonov, Valeriy O.</creator><creator>Fan, Zhijin</creator><creator>Slepukhin, Pavel А.</creator><creator>Bakulev, Vasiliy А.</creator><general>Springer US</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20201001</creationdate><title>The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides</title><author>Dianova, Lidiya N. ; Beryozkina, Tetyana V. ; Filimonov, Valeriy O. ; Fan, Zhijin ; Slepukhin, Pavel А. ; Bakulev, Vasiliy А.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c242t-ab07eff0f06504978f1e64103cf9be2f6eec8fc2ce82da940f2466cf74ebb3153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dianova, Lidiya N.</creatorcontrib><creatorcontrib>Beryozkina, Tetyana V.</creatorcontrib><creatorcontrib>Filimonov, Valeriy O.</creatorcontrib><creatorcontrib>Fan, Zhijin</creatorcontrib><creatorcontrib>Slepukhin, Pavel А.</creatorcontrib><creatorcontrib>Bakulev, Vasiliy А.</creatorcontrib><collection>CrossRef</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dianova, Lidiya N.</au><au>Beryozkina, Tetyana V.</au><au>Filimonov, Valeriy O.</au><au>Fan, Zhijin</au><au>Slepukhin, Pavel А.</au><au>Bakulev, Vasiliy А.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2020-10-01</date><risdate>2020</risdate><volume>56</volume><issue>10</issue><spage>1341</spage><epage>1347</epage><pages>1341-1347</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>The reaction of 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides with sulfonyl chlorides and acetyl and benzoyl chlorides is accompanied by the Dimroth rearrangement and proceeds regiospecifically with the formation of 5-arylamino-2-sulfonyl(acyl)-1,2,3-triazoles. The reaction mechanism was confirmed by the synthesis of the target products via the reaction of 5-arylamino-1,2,3-triazole-4-carbothioamides with sulfonyl and acyl chlorides.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-020-02820-3</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0009-3122
ispartof Chemistry of heterocyclic compounds (New York, N.Y. 1965), 2020-10, Vol.56 (10), p.1341-1347
issn 0009-3122
1573-8353
language eng
recordid cdi_crossref_primary_10_1007_s10593_020_02820_3
source Springer Link
subjects Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
title The tandem Dimroth rearrangement and sulfonylation/acylation as regioselective method for the synthesis of 5-arylamino-2-sulfonyland 2-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T19%3A16%3A37IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref_sprin&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20tandem%20Dimroth%20rearrangement%20and%20sulfonylation/acylation%20as%20regioselective%20method%20for%20the%20synthesis%20of%205-arylamino-2-sulfonyland%202-acyl-5-arylamino-1,2,3-triazole-4-carbothioamides&rft.jtitle=Chemistry%20of%20heterocyclic%20compounds%20(New%20York,%20N.Y.%201965)&rft.au=Dianova,%20Lidiya%20N.&rft.date=2020-10-01&rft.volume=56&rft.issue=10&rft.spage=1341&rft.epage=1347&rft.pages=1341-1347&rft.issn=0009-3122&rft.eissn=1573-8353&rft_id=info:doi/10.1007/s10593-020-02820-3&rft_dat=%3Ccrossref_sprin%3E10_1007_s10593_020_02820_3%3C/crossref_sprin%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c242t-ab07eff0f06504978f1e64103cf9be2f6eec8fc2ce82da940f2466cf74ebb3153%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true