Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer

Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient interme...

Full description

Saved in:
Bibliographic Details
Published in:Synlett 2015-04, Vol.26 (7), p.953-959
Main Authors: Panteleev, Jane, Maguire, Robert J., Kung, Daniel W.
Format: Article
Language:English
Subjects:
letter
Citations: 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-c277t-dead2bd62409383aa108e9a212e778d5797b67c496912d216164649e309e1e953
cites
container_end_page 959
container_issue 7
container_start_page 953
container_title Synlett
container_volume 26
creator Panteleev, Jane
Maguire, Robert J.
Kung, Daniel W.
description Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N -Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols.
doi_str_mv 10.1055/s-0034-1379961
format article
fullrecord <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_0034_1379961</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_0034_1379961</sourcerecordid><originalsourceid>FETCH-LOGICAL-c277t-dead2bd62409383aa108e9a212e778d5797b67c496912d216164649e309e1e953</originalsourceid><addsrcrecordid>eNp1kM1OAjEYRRujiYhuXfcFiv2bdrokRIWE6AJcN2XmGywOrWmLyby9ENiyupt7b04OQs-MThitqpdMKBWSMKGNUewGjZgUmnBq1C0aUSMUqTiT9-gh5x2lTNaGjtBy2v8MvSs-Bhw7_OFLilsIZBZDcT74sMVzKJBiMzQ9ZPznHV4EvPLlgFeHvoth6PE6uZA7SI_ornN9hqdLjtHX2-t6NifLz_fFbLokDde6kBZcyzet4vJIVQvnGK3BOM44aF23lTZ6o3QjjTKMt5wppqSSBgQ1wMBUYowm598mxZwTdPY3-b1Lg2XUnlzYbE8u7MXFcUDOg_LtYQ92Fw8pHAmv9f8BydxfMA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer</title><source>Thieme - Connect here FIRST to enable access</source><creator>Panteleev, Jane ; Maguire, Robert J. ; Kung, Daniel W.</creator><creatorcontrib>Panteleev, Jane ; Maguire, Robert J. ; Kung, Daniel W.</creatorcontrib><description>Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N -Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols.</description><identifier>ISSN: 0936-5214</identifier><identifier>EISSN: 1437-2096</identifier><identifier>DOI: 10.1055/s-0034-1379961</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><subject>letter</subject><ispartof>Synlett, 2015-04, Vol.26 (7), p.953-959</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c277t-dead2bd62409383aa108e9a212e778d5797b67c496912d216164649e309e1e953</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0034-1379961.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0034-1379961$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Panteleev, Jane</creatorcontrib><creatorcontrib>Maguire, Robert J.</creatorcontrib><creatorcontrib>Kung, Daniel W.</creatorcontrib><title>Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer</title><title>Synlett</title><addtitle>Synlett</addtitle><description>Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N -Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols.</description><subject>letter</subject><issn>0936-5214</issn><issn>1437-2096</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp1kM1OAjEYRRujiYhuXfcFiv2bdrokRIWE6AJcN2XmGywOrWmLyby9ENiyupt7b04OQs-MThitqpdMKBWSMKGNUewGjZgUmnBq1C0aUSMUqTiT9-gh5x2lTNaGjtBy2v8MvSs-Bhw7_OFLilsIZBZDcT74sMVzKJBiMzQ9ZPznHV4EvPLlgFeHvoth6PE6uZA7SI_ornN9hqdLjtHX2-t6NifLz_fFbLokDde6kBZcyzet4vJIVQvnGK3BOM44aF23lTZ6o3QjjTKMt5wppqSSBgQ1wMBUYowm598mxZwTdPY3-b1Lg2XUnlzYbE8u7MXFcUDOg_LtYQ92Fw8pHAmv9f8BydxfMA</recordid><startdate>20150401</startdate><enddate>20150401</enddate><creator>Panteleev, Jane</creator><creator>Maguire, Robert J.</creator><creator>Kung, Daniel W.</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20150401</creationdate><title>Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer</title><author>Panteleev, Jane ; Maguire, Robert J. ; Kung, Daniel W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c277t-dead2bd62409383aa108e9a212e778d5797b67c496912d216164649e309e1e953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>letter</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Panteleev, Jane</creatorcontrib><creatorcontrib>Maguire, Robert J.</creatorcontrib><creatorcontrib>Kung, Daniel W.</creatorcontrib><collection>CrossRef</collection><jtitle>Synlett</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Panteleev, Jane</au><au>Maguire, Robert J.</au><au>Kung, Daniel W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer</atitle><jtitle>Synlett</jtitle><addtitle>Synlett</addtitle><date>2015-04-01</date><risdate>2015</risdate><volume>26</volume><issue>7</issue><spage>953</spage><epage>959</epage><pages>953-959</pages><issn>0936-5214</issn><eissn>1437-2096</eissn><abstract>Abstract A convenient synthesis of N -substituted heterocycles from primary and secondary alcohols and N -sulfonyl heterocycles is described. The reaction proceeds through sulfonyl transfer and in situ formation of activated alcohol derivatives. The formation of alkyl sulfonates as transient intermediates mitigates challenges associated with isolation of these reactive species. N -Sulfonyl heteroarenes were found to be stable over prolonged time, and efficiently coupled to a variety of alcohols.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0034-1379961</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0936-5214
ispartof Synlett, 2015-04, Vol.26 (7), p.953-959
issn 0936-5214
1437-2096
language eng
recordid cdi_crossref_primary_10_1055_s_0034_1379961
source Thieme - Connect here FIRST to enable access
subjects letter
title Alkylation of Nitrogen-Containing Heterocycles via In Situ Sulfonyl Transfer
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-21T11%3A18%3A51IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-thieme_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Alkylation%20of%20Nitrogen-Containing%20Heterocycles%20via%20In%20Situ%20Sulfonyl%20Transfer&rft.jtitle=Synlett&rft.au=Panteleev,%20Jane&rft.date=2015-04-01&rft.volume=26&rft.issue=7&rft.spage=953&rft.epage=959&rft.pages=953-959&rft.issn=0936-5214&rft.eissn=1437-2096&rft_id=info:doi/10.1055/s-0034-1379961&rft_dat=%3Cthieme_cross%3E10_1055_s_0034_1379961%3C/thieme_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c277t-dead2bd62409383aa108e9a212e778d5797b67c496912d216164649e309e1e953%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