Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives

A variety of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives were achieved via a one-pot, three-component reaction from easily available methyl 2-perfluoroalkynoate, malononitrile (or ethyl cyanoacetate), and diverse cyclic 1,3-diketones. Moderate to good yields (...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Tetrahedron 2013-07, Vol.69 (30), p.6121-6128
Hauptverfasser: Bian, Linglin, Xu, Jiechao, Xie, Liqing, Chen, Jie, Deng, Hongmei, Shao, Min, Ding, Tianling, Zhang, Hui, Cao, Weiguo
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 6128
container_issue 30
container_start_page 6121
container_title Tetrahedron
container_volume 69
creator Bian, Linglin
Xu, Jiechao
Xie, Liqing
Chen, Jie
Deng, Hongmei
Shao, Min
Ding, Tianling
Zhang, Hui
Cao, Weiguo
description A variety of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives were achieved via a one-pot, three-component reaction from easily available methyl 2-perfluoroalkynoate, malononitrile (or ethyl cyanoacetate), and diverse cyclic 1,3-diketones. Moderate to good yields (up to 93%) were obtained in the presence of catalytic methylamine. This process went through a tandem Michael additionacyclization reaction and was mild and easily performed.
doi_str_mv 10.1016/j.tet.2013.05.053
format Article
fullrecord <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_miscellaneous_1744694441</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1744694441</sourcerecordid><originalsourceid>FETCH-proquest_miscellaneous_17446944413</originalsourceid><addsrcrecordid>eNqVjctOwzAQAH0AqeXxAdx85JBN17GTwhmB-gG9V1a6UdI63uB1KvL35MAPII00l5FGqReDpUHT7C5lplxWaGyJ9Yq9U1tEh-Cwwo16ELkgojGV3arp2CciaHmcOFLMWpaYe5JBNHe6Aj8OkcFCu_jVNfAPg4OJUhdmTuzDdQlQF02xL95g3SbfL-e0Ngdo-8SjJh1JnykNN5-HG8mTuu98EHr-86N6_fo8fhxgSvw9k-TTOEhLIfhIPMvJ7J1r3p1zxv4j_QUlZFJH</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1744694441</pqid></control><display><type>article</type><title>Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives</title><source>Elsevier ScienceDirect Journals</source><creator>Bian, Linglin ; Xu, Jiechao ; Xie, Liqing ; Chen, Jie ; Deng, Hongmei ; Shao, Min ; Ding, Tianling ; Zhang, Hui ; Cao, Weiguo</creator><creatorcontrib>Bian, Linglin ; Xu, Jiechao ; Xie, Liqing ; Chen, Jie ; Deng, Hongmei ; Shao, Min ; Ding, Tianling ; Zhang, Hui ; Cao, Weiguo</creatorcontrib><description>A variety of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives were achieved via a one-pot, three-component reaction from easily available methyl 2-perfluoroalkynoate, malononitrile (or ethyl cyanoacetate), and diverse cyclic 1,3-diketones. Moderate to good yields (up to 93%) were obtained in the presence of catalytic methylamine. This process went through a tandem Michael additionacyclization reaction and was mild and easily performed.</description><identifier>ISSN: 0040-4020</identifier><identifier>DOI: 10.1016/j.tet.2013.05.053</identifier><language>eng</language><subject>Catalysis ; Catalysts ; Derivatives ; Malononitrile ; Synthesis ; Tetrahedrons</subject><ispartof>Tetrahedron, 2013-07, Vol.69 (30), p.6121-6128</ispartof><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>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Bian, Linglin</creatorcontrib><creatorcontrib>Xu, Jiechao</creatorcontrib><creatorcontrib>Xie, Liqing</creatorcontrib><creatorcontrib>Chen, Jie</creatorcontrib><creatorcontrib>Deng, Hongmei</creatorcontrib><creatorcontrib>Shao, Min</creatorcontrib><creatorcontrib>Ding, Tianling</creatorcontrib><creatorcontrib>Zhang, Hui</creatorcontrib><creatorcontrib>Cao, Weiguo</creatorcontrib><title>Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives</title><title>Tetrahedron</title><description>A variety of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives were achieved via a one-pot, three-component reaction from easily available methyl 2-perfluoroalkynoate, malononitrile (or ethyl cyanoacetate), and diverse cyclic 1,3-diketones. Moderate to good yields (up to 93%) were obtained in the presence of catalytic methylamine. This process went through a tandem Michael additionacyclization reaction and was mild and easily performed.</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Derivatives</subject><subject>Malononitrile</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqVjctOwzAQAH0AqeXxAdx85JBN17GTwhmB-gG9V1a6UdI63uB1KvL35MAPII00l5FGqReDpUHT7C5lplxWaGyJ9Yq9U1tEh-Cwwo16ELkgojGV3arp2CciaHmcOFLMWpaYe5JBNHe6Aj8OkcFCu_jVNfAPg4OJUhdmTuzDdQlQF02xL95g3SbfL-e0Ngdo-8SjJh1JnykNN5-HG8mTuu98EHr-86N6_fo8fhxgSvw9k-TTOEhLIfhIPMvJ7J1r3p1zxv4j_QUlZFJH</recordid><startdate>20130701</startdate><enddate>20130701</enddate><creator>Bian, Linglin</creator><creator>Xu, Jiechao</creator><creator>Xie, Liqing</creator><creator>Chen, Jie</creator><creator>Deng, Hongmei</creator><creator>Shao, Min</creator><creator>Ding, Tianling</creator><creator>Zhang, Hui</creator><creator>Cao, Weiguo</creator><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20130701</creationdate><title>Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives</title><author>Bian, Linglin ; Xu, Jiechao ; Xie, Liqing ; Chen, Jie ; Deng, Hongmei ; Shao, Min ; Ding, Tianling ; Zhang, Hui ; Cao, Weiguo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-proquest_miscellaneous_17446944413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Catalysis</topic><topic>Catalysts</topic><topic>Derivatives</topic><topic>Malononitrile</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bian, Linglin</creatorcontrib><creatorcontrib>Xu, Jiechao</creatorcontrib><creatorcontrib>Xie, Liqing</creatorcontrib><creatorcontrib>Chen, Jie</creatorcontrib><creatorcontrib>Deng, Hongmei</creatorcontrib><creatorcontrib>Shao, Min</creatorcontrib><creatorcontrib>Ding, Tianling</creatorcontrib><creatorcontrib>Zhang, Hui</creatorcontrib><creatorcontrib>Cao, Weiguo</creatorcontrib><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bian, Linglin</au><au>Xu, Jiechao</au><au>Xie, Liqing</au><au>Chen, Jie</au><au>Deng, Hongmei</au><au>Shao, Min</au><au>Ding, Tianling</au><au>Zhang, Hui</au><au>Cao, Weiguo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives</atitle><jtitle>Tetrahedron</jtitle><date>2013-07-01</date><risdate>2013</risdate><volume>69</volume><issue>30</issue><spage>6121</spage><epage>6128</epage><pages>6121-6128</pages><issn>0040-4020</issn><abstract>A variety of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives were achieved via a one-pot, three-component reaction from easily available methyl 2-perfluoroalkynoate, malononitrile (or ethyl cyanoacetate), and diverse cyclic 1,3-diketones. Moderate to good yields (up to 93%) were obtained in the presence of catalytic methylamine. This process went through a tandem Michael additionacyclization reaction and was mild and easily performed.</abstract><doi>10.1016/j.tet.2013.05.053</doi></addata></record>
fulltext fulltext
identifier ISSN: 0040-4020
ispartof Tetrahedron, 2013-07, Vol.69 (30), p.6121-6128
issn 0040-4020
language eng
recordid cdi_proquest_miscellaneous_1744694441
source Elsevier ScienceDirect Journals
subjects Catalysis
Catalysts
Derivatives
Malononitrile
Synthesis
Tetrahedrons
title Three-component synthesis of 2-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom e ne derivatives
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-02T02%3A02%3A11IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Three-component%20synthesis%20of%202-amino-3-cyano-5-oxo-4-perfluoroalkyl-5,6,7,8-tetrahydro-4H-chrom%20e%20ne%20derivatives&rft.jtitle=Tetrahedron&rft.au=Bian,%20Linglin&rft.date=2013-07-01&rft.volume=69&rft.issue=30&rft.spage=6121&rft.epage=6128&rft.pages=6121-6128&rft.issn=0040-4020&rft_id=info:doi/10.1016/j.tet.2013.05.053&rft_dat=%3Cproquest%3E1744694441%3C/proquest%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1744694441&rft_id=info:pmid/&rfr_iscdi=true