Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles

A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2015-07, Vol.80 (14), p.7226-7234
Main Authors: Gazzola, Silvia, Beccalli, Egle M, Borelli, Tea, Castellano, Carlo, Chiacchio, Maria Assunta, Diamante, Daria, Broggini, Gianluigi
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Copper - chemistry
Halogenation
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Urea - 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-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3
cites cdi_FETCH-LOGICAL-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3
container_end_page 7234
container_issue 14
container_start_page 7226
container_title Journal of organic chemistry
container_volume 80
creator Gazzola, Silvia
Beccalli, Egle M
Borelli, Tea
Castellano, Carlo
Chiacchio, Maria Assunta
Diamante, Daria
Broggini, Gianluigi
description A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.
doi_str_mv 10.1021/acs.joc.5b01227
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1697217387</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1697217387</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3</originalsourceid><addsrcrecordid>eNp1kEFLwzAYhoMoOqdnb9KjIt2StEmaowx1A0FQdy5Z8lWrWTOTFKy_3simN0MgId_zvpAHoTOCJwRTMlU6TN6cnrAVJpSKPTQijOKcS1zuoxHGlOYF5cUROg7hDafFGDtER5QTQjBnIzTM3GYD_mKxuMxnKio7fIHJru27-xxelXUv0KnYui5zzc_r0A02W3pQIVNd4tatgXRNO3t0fYQsumyeYiqhNs06yJ_6VYhtTEOTzSGCd3rQFsIJOmiUDXC6O8doeXvzPJvn9w93i9n1fa4KKWOujTalUlIwQxinRGLZaFFqJYwUXOhSVrrhBde8VKwyGgQxVUVo0lGRkulijC62vRvvPnoIsV63QYO1qgPXh5pwKSgRRSUSOt2i2rsQPDT1xrdr5Yea4PrHd51818l3vfOdEue78n61BvPH_wpOwNUW2CZ736W__lv3DfQ1jCw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1697217387</pqid></control><display><type>article</type><title>Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles</title><source>Access via American Chemical Society</source><creator>Gazzola, Silvia ; Beccalli, Egle M ; Borelli, Tea ; Castellano, Carlo ; Chiacchio, Maria Assunta ; Diamante, Daria ; Broggini, Gianluigi</creator><creatorcontrib>Gazzola, Silvia ; Beccalli, Egle M ; Borelli, Tea ; Castellano, Carlo ; Chiacchio, Maria Assunta ; Diamante, Daria ; Broggini, Gianluigi</creatorcontrib><description>A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b01227</identifier><identifier>PMID: 26111065</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amides - chemistry ; Catalysis ; Copper - chemistry ; Halogenation ; Heterocyclic Compounds - chemical synthesis ; Heterocyclic Compounds - chemistry ; Molecular Structure ; Urea - chemistry</subject><ispartof>Journal of organic chemistry, 2015-07, Vol.80 (14), p.7226-7234</ispartof><rights>Copyright © American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3</citedby><cites>FETCH-LOGICAL-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26111065$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gazzola, Silvia</creatorcontrib><creatorcontrib>Beccalli, Egle M</creatorcontrib><creatorcontrib>Borelli, Tea</creatorcontrib><creatorcontrib>Castellano, Carlo</creatorcontrib><creatorcontrib>Chiacchio, Maria Assunta</creatorcontrib><creatorcontrib>Diamante, Daria</creatorcontrib><creatorcontrib>Broggini, Gianluigi</creatorcontrib><title>Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.</description><subject>Amides - chemistry</subject><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Halogenation</subject><subject>Heterocyclic Compounds - chemical synthesis</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Molecular Structure</subject><subject>Urea - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp1kEFLwzAYhoMoOqdnb9KjIt2StEmaowx1A0FQdy5Z8lWrWTOTFKy_3simN0MgId_zvpAHoTOCJwRTMlU6TN6cnrAVJpSKPTQijOKcS1zuoxHGlOYF5cUROg7hDafFGDtER5QTQjBnIzTM3GYD_mKxuMxnKio7fIHJru27-xxelXUv0KnYui5zzc_r0A02W3pQIVNd4tatgXRNO3t0fYQsumyeYiqhNs06yJ_6VYhtTEOTzSGCd3rQFsIJOmiUDXC6O8doeXvzPJvn9w93i9n1fa4KKWOujTalUlIwQxinRGLZaFFqJYwUXOhSVrrhBde8VKwyGgQxVUVo0lGRkulijC62vRvvPnoIsV63QYO1qgPXh5pwKSgRRSUSOt2i2rsQPDT1xrdr5Yea4PrHd51818l3vfOdEue78n61BvPH_wpOwNUW2CZ736W__lv3DfQ1jCw</recordid><startdate>20150717</startdate><enddate>20150717</enddate><creator>Gazzola, Silvia</creator><creator>Beccalli, Egle M</creator><creator>Borelli, Tea</creator><creator>Castellano, Carlo</creator><creator>Chiacchio, Maria Assunta</creator><creator>Diamante, Daria</creator><creator>Broggini, Gianluigi</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></search><sort><creationdate>20150717</creationdate><title>Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles</title><author>Gazzola, Silvia ; Beccalli, Egle M ; Borelli, Tea ; Castellano, Carlo ; Chiacchio, Maria Assunta ; Diamante, Daria ; Broggini, Gianluigi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Amides - chemistry</topic><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Halogenation</topic><topic>Heterocyclic Compounds - chemical synthesis</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Molecular Structure</topic><topic>Urea - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gazzola, Silvia</creatorcontrib><creatorcontrib>Beccalli, Egle M</creatorcontrib><creatorcontrib>Borelli, Tea</creatorcontrib><creatorcontrib>Castellano, Carlo</creatorcontrib><creatorcontrib>Chiacchio, Maria Assunta</creatorcontrib><creatorcontrib>Diamante, Daria</creatorcontrib><creatorcontrib>Broggini, Gianluigi</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><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gazzola, Silvia</au><au>Beccalli, Egle M</au><au>Borelli, Tea</au><au>Castellano, Carlo</au><au>Chiacchio, Maria Assunta</au><au>Diamante, Daria</au><au>Broggini, Gianluigi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-07-17</date><risdate>2015</risdate><volume>80</volume><issue>14</issue><spage>7226</spage><epage>7234</epage><pages>7226-7234</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A highly effective synthesis of haloalkylidene-substituted heterocycles by copper­(II)-catalyzed cyclization of alkynyl ureas and secondary amides has been developed. The reaction, which involves a catalytic amount of CuCl2 and a stoichiometric amount of N-halosuccinimide, occurs selectively through an alkoxyhalogenation process. Alternatively, alkoxychlorination and alkoxybromination reactions can be performed working solely with stoichiometric CuCl2 and CuBr2, respectively.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26111065</pmid><doi>10.1021/acs.joc.5b01227</doi><tpages>9</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2015-07, Vol.80 (14), p.7226-7234
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1697217387
source Access via American Chemical Society
subjects Amides - chemistry
Catalysis
Copper - chemistry
Halogenation
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Molecular Structure
Urea - chemistry
title Copper(II)-Catalyzed Alkoxyhalogenation of Alkynyl Ureas and Amides as a Route to Haloalkylidene-Substituted Heterocycles
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T00%3A43%3A40IST&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=Copper(II)-Catalyzed%20Alkoxyhalogenation%20of%20Alkynyl%20Ureas%20and%20Amides%20as%20a%20Route%20to%20Haloalkylidene-Substituted%20Heterocycles&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Gazzola,%20Silvia&rft.date=2015-07-17&rft.volume=80&rft.issue=14&rft.spage=7226&rft.epage=7234&rft.pages=7226-7234&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.5b01227&rft_dat=%3Cproquest_cross%3E1697217387%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a399t-cdcd4aa975d15621909fc74ca7d9767c498cf636c64a58dce71d88121228145c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1697217387&rft_id=info:pmid/26111065&rfr_iscdi=true