Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c

Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternar...

Full description

Saved in:
Bibliographic Details
Main Authors: Babu, K. Naresh, Kinthada, Lakshmana K, Ghosh, Santanu, Bisai, Alakesh
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 1655
container_issue 43
container_start_page 1641
container_title
container_volume 13
creator Babu, K. Naresh
Kinthada, Lakshmana K
Ghosh, Santanu
Bisai, Alakesh
description Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternary center at the pseudobenzylic position in high yields. An expeditious approach to a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage sharing an all-carbon quaternary center at the pseudobenzylic position has been developed via Lewis acid-catalyzed F-C alkylations.
doi_str_mv 10.1039/c5ob01670c
format article
fullrecord <record><control><sourceid>rsc</sourceid><recordid>TN_cdi_rsc_primary_c5ob01670c</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c5ob01670c</sourcerecordid><originalsourceid>FETCH-rsc_primary_c5ob01670c3</originalsourceid><addsrcrecordid>eNqFkk1v00AQhg0CiVK4cEcabiDV7jrOB-mxbqJGiA9B7tF0dxwv2Xit2W2IOfGb-EnwRxiniCJVgtOOdmbf93lHmyTPcpXlqpie6pG_Uvl4ovT95CgfTiapGhXTB3_qgXqUPA7hs1L5dDIeHt37eWnXtetA17T1gRzpaHcEoWtiTcEG8BUYuyW2Ggap39vGeEcBvthYA0KZFqdlOvrx7Ts422xwTbCzCHO2ZMilJWMVA6DbdA6j9c1B745OkdadYb_v0r9ay1rcW2yJQQpDxmqMZCB6-MC-ohA8wzKDNxmUNTaGMdCmRgbfgLCD1xqDWPaOvdRYidO55Vgb7LJZn5R9I7HCdds62lITkTuwTeV5e4CFl7NPi1eAO7QOrxydwWwvOPYw6qBlr8lcM4UTWR8y6ijNrzdPDUY8gXdvP0JoeycUyvKihFyNxoOpAgGGfKjGg9fDDOaSRKwOl5q7IOrOrxnbWvB6JaGCcjEHmfOSjYFu8W9wIRDBxfvFGdz9Ck-ShxW6QE9_n8fJ8_lsWV6mHPSqlTySe3U7XhwnL_7VX7WmKv6n8QsuqtfQ</addsrcrecordid><sourcetype>Enrichment Source</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c</title><source>Royal Society of Chemistry</source><creator>Babu, K. Naresh ; Kinthada, Lakshmana K ; Ghosh, Santanu ; Bisai, Alakesh</creator><creatorcontrib>Babu, K. Naresh ; Kinthada, Lakshmana K ; Ghosh, Santanu ; Bisai, Alakesh</creatorcontrib><description>Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternary center at the pseudobenzylic position in high yields. An expeditious approach to a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage sharing an all-carbon quaternary center at the pseudobenzylic position has been developed via Lewis acid-catalyzed F-C alkylations.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c5ob01670c</identifier><language>eng</language><creationdate>2015-10</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids></links><search><creatorcontrib>Babu, K. Naresh</creatorcontrib><creatorcontrib>Kinthada, Lakshmana K</creatorcontrib><creatorcontrib>Ghosh, Santanu</creatorcontrib><creatorcontrib>Bisai, Alakesh</creatorcontrib><title>Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c</title><description>Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternary center at the pseudobenzylic position in high yields. An expeditious approach to a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage sharing an all-carbon quaternary center at the pseudobenzylic position has been developed via Lewis acid-catalyzed F-C alkylations.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkk1v00AQhg0CiVK4cEcabiDV7jrOB-mxbqJGiA9B7tF0dxwv2Xit2W2IOfGb-EnwRxiniCJVgtOOdmbf93lHmyTPcpXlqpie6pG_Uvl4ovT95CgfTiapGhXTB3_qgXqUPA7hs1L5dDIeHt37eWnXtetA17T1gRzpaHcEoWtiTcEG8BUYuyW2Ggap39vGeEcBvthYA0KZFqdlOvrx7Ts422xwTbCzCHO2ZMilJWMVA6DbdA6j9c1B745OkdadYb_v0r9ay1rcW2yJQQpDxmqMZCB6-MC-ohA8wzKDNxmUNTaGMdCmRgbfgLCD1xqDWPaOvdRYidO55Vgb7LJZn5R9I7HCdds62lITkTuwTeV5e4CFl7NPi1eAO7QOrxydwWwvOPYw6qBlr8lcM4UTWR8y6ijNrzdPDUY8gXdvP0JoeycUyvKihFyNxoOpAgGGfKjGg9fDDOaSRKwOl5q7IOrOrxnbWvB6JaGCcjEHmfOSjYFu8W9wIRDBxfvFGdz9Ck-ShxW6QE9_n8fJ8_lsWV6mHPSqlTySe3U7XhwnL_7VX7WmKv6n8QsuqtfQ</recordid><startdate>20151028</startdate><enddate>20151028</enddate><creator>Babu, K. Naresh</creator><creator>Kinthada, Lakshmana K</creator><creator>Ghosh, Santanu</creator><creator>Bisai, Alakesh</creator><scope/></search><sort><creationdate>20151028</creationdate><title>Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c</title><author>Babu, K. Naresh ; Kinthada, Lakshmana K ; Ghosh, Santanu ; Bisai, Alakesh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c5ob01670c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Babu, K. Naresh</creatorcontrib><creatorcontrib>Kinthada, Lakshmana K</creatorcontrib><creatorcontrib>Ghosh, Santanu</creatorcontrib><creatorcontrib>Bisai, Alakesh</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Babu, K. Naresh</au><au>Kinthada, Lakshmana K</au><au>Ghosh, Santanu</au><au>Bisai, Alakesh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c</atitle><date>2015-10-28</date><risdate>2015</risdate><volume>13</volume><issue>43</issue><spage>1641</spage><epage>1655</epage><pages>1641-1655</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage having an all-carbon quaternary center at the pseudobenzylic position in high yields. An expeditious approach to a variety of dimeric 2-oxindoles with a C-3/C-5′ linkage sharing an all-carbon quaternary center at the pseudobenzylic position has been developed via Lewis acid-catalyzed F-C alkylations.</abstract><doi>10.1039/c5ob01670c</doi><tpages>15</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1477-0520
ispartof
issn 1477-0520
1477-0539
language eng
recordid cdi_rsc_primary_c5ob01670c
source Royal Society of Chemistry
title Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindolesThis paper is dedicated to Professor T. K. Chandrasekhar on the occasion of his 60th Birthday.Electronic supplementary information (ESI) available: Experimental procedures, characterization data, NMR spectra. CCDC 1056290 and 1406284. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ob01670c
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-13T15%3A47%3A01IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-rsc&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Highly%20chemoselective%20synthesis%20of%20dimeric%202-oxindoles%20with%20a%20C-3/C-5%E2%80%B2%20linkage%20via%20Friedel-Crafts%20alkylations%20of%202-oxindoles%20with%203-hydroxy-2-oxindolesThis%20paper%20is%20dedicated%20to%20Professor%20T.%20K.%20Chandrasekhar%20on%20the%20occasion%20of%20his%2060th%20Birthday.Electronic%20supplementary%20information%20(ESI)%20available:%20Experimental%20procedures,%20characterization%20data,%20NMR%20spectra.%20CCDC%201056290%20and%201406284.%20For%20ESI%20and%20crystallographic%20data%20in%20CIF%20or%20other%20electronic%20format%20see%20DOI:%2010.1039/c5ob01670c&rft.au=Babu,%20K.%20Naresh&rft.date=2015-10-28&rft.volume=13&rft.issue=43&rft.spage=1641&rft.epage=1655&rft.pages=1641-1655&rft.issn=1477-0520&rft.eissn=1477-0539&rft_id=info:doi/10.1039/c5ob01670c&rft_dat=%3Crsc%3Ec5ob01670c%3C/rsc%3E%3Cgrp_id%3Ecdi_FETCH-rsc_primary_c5ob01670c3%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