Loading…

Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles

A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueo...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2005-03, Vol.7 (5), p.863-866
Main Authors: Poondra, Rajamohan R, Turner, Nicholas J
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-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583
cites cdi_FETCH-LOGICAL-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583
container_end_page 866
container_issue 5
container_start_page 863
container_title Organic letters
container_volume 7
creator Poondra, Rajamohan R
Turner, Nicholas J
description A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.
doi_str_mv 10.1021/ol0473804
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_67459716</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>67459716</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583</originalsourceid><addsrcrecordid>eNptkMtKAzEUhoMoVqsLX0CyUXAxmkwmyYy7sbRaqBS8rIc0SSFlZlKTGbWC4NbX9ElML9SNq3P7zn84PwAnGF1iFOMrW6KEkxQlO-AA05hEHNF4d5sz1AGH3s8QwqGT7YMOpjzmCUMH4PPeSGffxKuOcu-Nb7SCj_ql1XVjRAnzyigNb2yt4MC6SjTG1lCEalg3TlS21LIthVtxq-H1z9c3zOGDmBsF-wFawMbCQVvL5VSU5iMcGL-bWoVdfwT2pqL0-ngTu-B50H_q3UWj8e2wl48iQXjWRIlimEyyhFGRMj2ZMplSynkaZxnBAiUJS2WsUKY5JYQomU6pIlKlGeMoRjQlXXC-1p07G37zTVEZL3VZilrb1heMJzTjmAXwYg0GU7x3elrMnamEWxQYFUuvi63XgT3diLaTSqs_cmNuAM7WgJC-mNnWhf_9P0K_iOeGMg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>67459716</pqid></control><display><type>article</type><title>Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Poondra, Rajamohan R ; Turner, Nicholas J</creator><creatorcontrib>Poondra, Rajamohan R ; Turner, Nicholas J</creatorcontrib><description>A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol0473804</identifier><identifier>PMID: 15727460</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2005-03, Vol.7 (5), p.863-866</ispartof><rights>Copyright © 2005 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583</citedby><cites>FETCH-LOGICAL-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583</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/15727460$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Poondra, Rajamohan R</creatorcontrib><creatorcontrib>Turner, Nicholas J</creatorcontrib><title>Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNptkMtKAzEUhoMoVqsLX0CyUXAxmkwmyYy7sbRaqBS8rIc0SSFlZlKTGbWC4NbX9ElML9SNq3P7zn84PwAnGF1iFOMrW6KEkxQlO-AA05hEHNF4d5sz1AGH3s8QwqGT7YMOpjzmCUMH4PPeSGffxKuOcu-Nb7SCj_ql1XVjRAnzyigNb2yt4MC6SjTG1lCEalg3TlS21LIthVtxq-H1z9c3zOGDmBsF-wFawMbCQVvL5VSU5iMcGL-bWoVdfwT2pqL0-ngTu-B50H_q3UWj8e2wl48iQXjWRIlimEyyhFGRMj2ZMplSynkaZxnBAiUJS2WsUKY5JYQomU6pIlKlGeMoRjQlXXC-1p07G37zTVEZL3VZilrb1heMJzTjmAXwYg0GU7x3elrMnamEWxQYFUuvi63XgT3diLaTSqs_cmNuAM7WgJC-mNnWhf_9P0K_iOeGMg</recordid><startdate>20050303</startdate><enddate>20050303</enddate><creator>Poondra, Rajamohan R</creator><creator>Turner, Nicholas J</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050303</creationdate><title>Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles</title><author>Poondra, Rajamohan R ; Turner, Nicholas J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Poondra, Rajamohan R</creatorcontrib><creatorcontrib>Turner, Nicholas J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Poondra, Rajamohan R</au><au>Turner, Nicholas J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2005-03-03</date><risdate>2005</risdate><volume>7</volume><issue>5</issue><spage>863</spage><epage>866</epage><pages>863-866</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A general method has been developed for the synthesis of N-substituted oxindoles. The two-step process involves initial microwave-assisted amide bond formation between 2-halo-arylacetic acids and various alkylamines and anilines, followed by a palladium-catalyzed intramolecular amidation under aqueous conditions. In the case of alkylamines, the procedure can be carried out as a one-pot process without isolation of the intermediate amide.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15727460</pmid><doi>10.1021/ol0473804</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2005-03, Vol.7 (5), p.863-866
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_67459716
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Microwave-Assisted Sequential Amide Bond Formation and Intramolecular Amidation:  A Rapid Entry to Functionalized Oxindoles
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T16%3A10%3A32IST&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=Microwave-Assisted%20Sequential%20Amide%20Bond%20Formation%20and%20Intramolecular%20Amidation:%E2%80%89%20A%20Rapid%20Entry%20to%20Functionalized%20Oxindoles&rft.jtitle=Organic%20letters&rft.au=Poondra,%20Rajamohan%20R&rft.date=2005-03-03&rft.volume=7&rft.issue=5&rft.spage=863&rft.epage=866&rft.pages=863-866&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol0473804&rft_dat=%3Cproquest_cross%3E67459716%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a379t-4d613b9465a86ebf6c85577829931a04468c2d09e75333dc8f5d3cd8967020583%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=67459716&rft_id=info:pmid/15727460&rfr_iscdi=true