Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group

An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluorom...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2021-02, Vol.2021 (5), p.788-793
Main Authors: Chen, Zheng‐Jun, Liang, Wei, Chen, Zhuo, Chen, Lin
Format: Article
Language:English
Subjects:
[3+2] Cycloaddition
Ammonium salts
Catalysts
Chemical synthesis
Cross coupling
Cycloaddition
Heterocycles
Imines
Phase-transfer catalysis
Quaternary ammonium salts
Rapid synthesis
Reaction mechanisms
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-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73
cites cdi_FETCH-LOGICAL-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73
container_end_page 793
container_issue 5
container_start_page 788
container_title European journal of organic chemistry
container_volume 2021
creator Chen, Zheng‐Jun
Liang, Wei
Chen, Zhuo
Chen, Lin
description An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s in good yields and with excellent diastereoselectivities. The preparative‐scale reaction in conjunction with the optimized Suzuki–Miyaura cross‐coupling derivatizations of the product give prominence to application prospect of this methodology. The investigation on the reaction mechanism implies that the real catalyst in the cycloaddition might be tetrahexylammonium carbonate. A phase‐transfer catalytic 1,3‐dipolar [3+2] cycloaddition grants rapid generation of various trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s that might be of great utility for drug discovery. The gram‐scale reaction in conjunction with the derivatizations of the product demonstrate the synthetic potential of this methodology. The reaction mechanism is also discussed.
doi_str_mv 10.1002/ejoc.202001409
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2486404733</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2486404733</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73</originalsourceid><addsrcrecordid>eNqFkc9uEzEQxlcIJErhytkS126w114n5oaipn9UKVWTStxWrj1mHW3Wy9irsjceoW_T9-FJcJQKjpzmG-n7zWjmK4qPjM4YpdVn2AUzq2hFKRNUvSpOGFWqpFLR11kLLkqm-Le3xbsYd5RSJSU7KZ5vWx3h96-nLeo-OkCy1El3U_KGbBLqBN-nL-ROD96SzdSnFqKPJDiyGTyGzK3GCJZcQgIMZjIdxDNy1WfswFry6FNLVmFEkhfhXpswtAEhZnIzGuN7v_cWzsjthBg6b32fm_VP39vQZaV7S7boXTcGDHtI7dSRCwzj8L5443QX4cNLPS3uV-fb5WV5s764Wn69KQ1nc1UyueAPUnBtoDaSVTWzSjvgtaoNWLFwtrJy7ii3fCEgP07ZB1m5mismJNg5Py0-HecOGH6MEFOzy8f0eWVTiYUUVMw5z67Z0WUwxIjgmgH9XuPUMNocwmkO4TR_w8mAOgKPvoPpP-7m_Hq9_Mf-Ack2mpE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2486404733</pqid></control><display><type>article</type><title>Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group</title><source>Wiley</source><creator>Chen, Zheng‐Jun ; Liang, Wei ; Chen, Zhuo ; Chen, Lin</creator><creatorcontrib>Chen, Zheng‐Jun ; Liang, Wei ; Chen, Zhuo ; Chen, Lin</creatorcontrib><description>An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s in good yields and with excellent diastereoselectivities. The preparative‐scale reaction in conjunction with the optimized Suzuki–Miyaura cross‐coupling derivatizations of the product give prominence to application prospect of this methodology. The investigation on the reaction mechanism implies that the real catalyst in the cycloaddition might be tetrahexylammonium carbonate. A phase‐transfer catalytic 1,3‐dipolar [3+2] cycloaddition grants rapid generation of various trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s that might be of great utility for drug discovery. The gram‐scale reaction in conjunction with the derivatizations of the product demonstrate the synthetic potential of this methodology. The reaction mechanism is also discussed.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202001409</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>[3+2] Cycloaddition ; Ammonium salts ; Catalysts ; Chemical synthesis ; Cross coupling ; Cycloaddition ; Heterocycles ; Imines ; Phase-transfer catalysis ; Quaternary ammonium salts ; Rapid synthesis ; Reaction mechanisms</subject><ispartof>European journal of organic chemistry, 2021-02, Vol.2021 (5), p.788-793</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73</citedby><cites>FETCH-LOGICAL-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73</cites><orcidid>0000-0002-8553-5754</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202001409$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202001409$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,786,790,27957,27958,50923,51032</link.rule.ids></links><search><creatorcontrib>Chen, Zheng‐Jun</creatorcontrib><creatorcontrib>Liang, Wei</creatorcontrib><creatorcontrib>Chen, Zhuo</creatorcontrib><creatorcontrib>Chen, Lin</creatorcontrib><title>Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group</title><title>European journal of organic chemistry</title><description>An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s in good yields and with excellent diastereoselectivities. The preparative‐scale reaction in conjunction with the optimized Suzuki–Miyaura cross‐coupling derivatizations of the product give prominence to application prospect of this methodology. The investigation on the reaction mechanism implies that the real catalyst in the cycloaddition might be tetrahexylammonium carbonate. A phase‐transfer catalytic 1,3‐dipolar [3+2] cycloaddition grants rapid generation of various trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s that might be of great utility for drug discovery. The gram‐scale reaction in conjunction with the derivatizations of the product demonstrate the synthetic potential of this methodology. The reaction mechanism is also discussed.</description><subject>[3+2] Cycloaddition</subject><subject>Ammonium salts</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Cross coupling</subject><subject>Cycloaddition</subject><subject>Heterocycles</subject><subject>Imines</subject><subject>Phase-transfer catalysis</subject><subject>Quaternary ammonium salts</subject><subject>Rapid synthesis</subject><subject>Reaction mechanisms</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkc9uEzEQxlcIJErhytkS126w114n5oaipn9UKVWTStxWrj1mHW3Wy9irsjceoW_T9-FJcJQKjpzmG-n7zWjmK4qPjM4YpdVn2AUzq2hFKRNUvSpOGFWqpFLR11kLLkqm-Le3xbsYd5RSJSU7KZ5vWx3h96-nLeo-OkCy1El3U_KGbBLqBN-nL-ROD96SzdSnFqKPJDiyGTyGzK3GCJZcQgIMZjIdxDNy1WfswFry6FNLVmFEkhfhXpswtAEhZnIzGuN7v_cWzsjthBg6b32fm_VP39vQZaV7S7boXTcGDHtI7dSRCwzj8L5443QX4cNLPS3uV-fb5WV5s764Wn69KQ1nc1UyueAPUnBtoDaSVTWzSjvgtaoNWLFwtrJy7ii3fCEgP07ZB1m5mismJNg5Py0-HecOGH6MEFOzy8f0eWVTiYUUVMw5z67Z0WUwxIjgmgH9XuPUMNocwmkO4TR_w8mAOgKPvoPpP-7m_Hq9_Mf-Ack2mpE</recordid><startdate>20210205</startdate><enddate>20210205</enddate><creator>Chen, Zheng‐Jun</creator><creator>Liang, Wei</creator><creator>Chen, Zhuo</creator><creator>Chen, Lin</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-8553-5754</orcidid></search><sort><creationdate>20210205</creationdate><title>Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group</title><author>Chen, Zheng‐Jun ; Liang, Wei ; Chen, Zhuo ; Chen, Lin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>[3+2] Cycloaddition</topic><topic>Ammonium salts</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Cross coupling</topic><topic>Cycloaddition</topic><topic>Heterocycles</topic><topic>Imines</topic><topic>Phase-transfer catalysis</topic><topic>Quaternary ammonium salts</topic><topic>Rapid synthesis</topic><topic>Reaction mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Zheng‐Jun</creatorcontrib><creatorcontrib>Liang, Wei</creatorcontrib><creatorcontrib>Chen, Zhuo</creatorcontrib><creatorcontrib>Chen, Lin</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Zheng‐Jun</au><au>Liang, Wei</au><au>Chen, Zhuo</au><au>Chen, Lin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-02-05</date><risdate>2021</risdate><volume>2021</volume><issue>5</issue><spage>788</spage><epage>793</epage><pages>788-793</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient and practical 1,3‐dipolar [3+2] cycloaddition of N‐2,2,2‐trifluoroethylisatin ketimines and maleimides has been achieved through phase‐transfer catalytic process by using the cheap quaternary ammonium salt as a catalyst. The strategy grants rapid generation of various complex trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s in good yields and with excellent diastereoselectivities. The preparative‐scale reaction in conjunction with the optimized Suzuki–Miyaura cross‐coupling derivatizations of the product give prominence to application prospect of this methodology. The investigation on the reaction mechanism implies that the real catalyst in the cycloaddition might be tetrahexylammonium carbonate. A phase‐transfer catalytic 1,3‐dipolar [3+2] cycloaddition grants rapid generation of various trifluoromethyl spiro‐fused[succinimide‐pyrrolidine‐oxindole]s that might be of great utility for drug discovery. The gram‐scale reaction in conjunction with the derivatizations of the product demonstrate the synthetic potential of this methodology. The reaction mechanism is also discussed.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202001409</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-8553-5754</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European journal of organic chemistry, 2021-02, Vol.2021 (5), p.788-793
issn 1434-193X
1099-0690
language eng
recordid cdi_proquest_journals_2486404733
source Wiley
subjects [3+2] Cycloaddition
Ammonium salts
Catalysts
Chemical synthesis
Cross coupling
Cycloaddition
Heterocycles
Imines
Phase-transfer catalysis
Quaternary ammonium salts
Rapid synthesis
Reaction mechanisms
title Phase‐Transfer Catalytic Strategy: Rapid Synthesis of Spiro‐Fused Heterocycles, Integrated with Four Pharmacophores‐Succinimide, Pyrrolidine, Oxindole, and Trifluoromethyl Group
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-09-21T14%3A11%3A31IST&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=Phase%E2%80%90Transfer%20Catalytic%20Strategy:%20Rapid%20Synthesis%20of%20Spiro%E2%80%90Fused%20Heterocycles,%20Integrated%20with%20Four%20Pharmacophores%E2%80%90Succinimide,%20Pyrrolidine,%20Oxindole,%20and%20Trifluoromethyl%20Group&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Chen,%20Zheng%E2%80%90Jun&rft.date=2021-02-05&rft.volume=2021&rft.issue=5&rft.spage=788&rft.epage=793&rft.pages=788-793&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.202001409&rft_dat=%3Cproquest_cross%3E2486404733%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3179-1683b643ace5c61251d9afe3595ced48fd2d67f03d384e0149db62f539146ed73%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2486404733&rft_id=info:pmid/&rfr_iscdi=true