BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines

BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines

Abstract A safe and convenient synthetic method to anti -β-( N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super­ acid...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Synthesis (Stuttgart) 2020-02, Vol.52 (4), p.602-608
Hauptverfasser: Xu, Chuangchuang, Lu, Yang, Xu, Kaini, Xu, Jiaxi
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 608
container_issue 4
container_start_page 602
container_title Synthesis (Stuttgart)
container_volume 52
creator Xu, Chuangchuang
Lu, Yang
Xu, Kaini
Xu, Jiaxi
description Abstract A safe and convenient synthetic method to anti -β-( N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super­ acid H[B(OEt)F 3 ], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti -β-( N -arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.
doi_str_mv 10.1055/s-0039-1690243
format Article
fullrecord <record><control><sourceid>thieme_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1055_s_0039_1690243</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1055_s_0039_1690243</sourcerecordid><originalsourceid>FETCH-LOGICAL-c1223-5cc4c25c5e532e2b4d717346c4dce7ea46a27e7396a0a18d1600218650a975f33</originalsourceid><addsrcrecordid>eNp1kL1OwzAUhS0EEqWwMnuEwcU_SdyMpbSAVFGpgMQWuc5N6yq1KzuIhvfhAWBh5wH6TPRPbExnOPf7dHUQOme0xWgcXwVCqUgJS1LKI3GAGiwSknBGXw5RY1vJdpsdo5MQZpRSyUXaQB_XffHzPexVnHRVpcr6HXL8WNtqCsEE7AqsbGXI6otcPJCOr0s1N9ZdktUnmda5d8vamsqbEgIe13gEE-PIGsnxjVGhAg8uLECbwmg8MnaChwuwm1yLxdbnlsYrC4QTrfzY_dneTDXFHWtKYyGcoqNClQHO9tlEz_3eU_eODIa3993OgGjGuSCx1pHmsY4hFhz4OMolkyJKdJRrkKCiRHEJUqSJooq1c5ZQylk7ialKZVwI0UStnVd7F4KHIlt4M1e-zhjNNiNnIdssme1HXgNkB1RTA3PIZu7V2_WH_93_ApVbgSM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines</title><source>Thieme Connect Journals</source><creator>Xu, Chuangchuang ; Lu, Yang ; Xu, Kaini ; Xu, Jiaxi</creator><creatorcontrib>Xu, Chuangchuang ; Lu, Yang ; Xu, Kaini ; Xu, Jiaxi</creatorcontrib><description>Abstract A safe and convenient synthetic method to anti -β-( N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super­ acid H[B(OEt)F 3 ], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti -β-( N -arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0039-1690243</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2020-02, Vol.52 (4), p.602-608</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c1223-5cc4c25c5e532e2b4d717346c4dce7ea46a27e7396a0a18d1600218650a975f33</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-0039-1690243.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0039-1690243$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3004,3005,27901,27902,54534,54535</link.rule.ids></links><search><creatorcontrib>Xu, Chuangchuang</creatorcontrib><creatorcontrib>Lu, Yang</creatorcontrib><creatorcontrib>Xu, Kaini</creatorcontrib><creatorcontrib>Xu, Jiaxi</creatorcontrib><title>BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract A safe and convenient synthetic method to anti -β-( N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super­ acid H[B(OEt)F 3 ], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti -β-( N -arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp1kL1OwzAUhS0EEqWwMnuEwcU_SdyMpbSAVFGpgMQWuc5N6yq1KzuIhvfhAWBh5wH6TPRPbExnOPf7dHUQOme0xWgcXwVCqUgJS1LKI3GAGiwSknBGXw5RY1vJdpsdo5MQZpRSyUXaQB_XffHzPexVnHRVpcr6HXL8WNtqCsEE7AqsbGXI6otcPJCOr0s1N9ZdktUnmda5d8vamsqbEgIe13gEE-PIGsnxjVGhAg8uLECbwmg8MnaChwuwm1yLxdbnlsYrC4QTrfzY_dneTDXFHWtKYyGcoqNClQHO9tlEz_3eU_eODIa3993OgGjGuSCx1pHmsY4hFhz4OMolkyJKdJRrkKCiRHEJUqSJooq1c5ZQylk7ialKZVwI0UStnVd7F4KHIlt4M1e-zhjNNiNnIdssme1HXgNkB1RTA3PIZu7V2_WH_93_ApVbgSM</recordid><startdate>202002</startdate><enddate>202002</enddate><creator>Xu, Chuangchuang</creator><creator>Lu, Yang</creator><creator>Xu, Kaini</creator><creator>Xu, Jiaxi</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>202002</creationdate><title>BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines</title><author>Xu, Chuangchuang ; Lu, Yang ; Xu, Kaini ; Xu, Jiaxi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1223-5cc4c25c5e532e2b4d717346c4dce7ea46a27e7396a0a18d1600218650a975f33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Chuangchuang</creatorcontrib><creatorcontrib>Lu, Yang</creatorcontrib><creatorcontrib>Xu, Kaini</creatorcontrib><creatorcontrib>Xu, Jiaxi</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xu, Chuangchuang</au><au>Lu, Yang</au><au>Xu, Kaini</au><au>Xu, Jiaxi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2020-02</date><risdate>2020</risdate><volume>52</volume><issue>4</issue><spage>602</spage><epage>608</epage><pages>602-608</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract A safe and convenient synthetic method to anti -β-( N -arylamino)-α-hydroxynitriles from 3-aryloxirane-2-carbonitriles and anilines was developed under the catalysis of BF 3 ·OEt 2 in ethanol. In this method, BF 3 ·OEt 2 first reacts with ethanol to produce the true catalyst of super­ acid H[B(OEt)F 3 ], followed by an acid-catalyzed regio- and diastereospecific ring opening of oxirane-2-carbonitriles with anilines, generating anti -β-( N -arylamino)-α-hydroxynitriles. The method features the advantages of non-metal catalysis, short reaction times, and easy operation, and uses an environmentally friendly solvent.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0039-1690243</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0039-7881
ispartof Synthesis (Stuttgart), 2020-02, Vol.52 (4), p.602-608
issn 0039-7881
1437-210X
language eng
recordid cdi_crossref_primary_10_1055_s_0039_1690243
source Thieme Connect Journals
title BF3·OEt2-Catalyzed Synthesis of anti-β-(N-Arylamino)-α-hydroxynitriles by Regio- and Diastereospecific Ring Opening of 3-Aryloxirane-2-carbonitriles with Anilines
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-07T23%3A59%3A56IST&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=BF3%C2%B7OEt2-Catalyzed%20Synthesis%20of%20anti-%CE%B2-(N-Arylamino)-%CE%B1-hydroxynitriles%20by%20Regio-%20and%20Diastereospecific%20Ring%20Opening%20of%203-Aryloxirane-2-carbonitriles%20with%20Anilines&rft.jtitle=Synthesis%20(Stuttgart)&rft.au=Xu,%20Chuangchuang&rft.date=2020-02&rft.volume=52&rft.issue=4&rft.spage=602&rft.epage=608&rft.pages=602-608&rft.issn=0039-7881&rft.eissn=1437-210X&rft_id=info:doi/10.1055/s-0039-1690243&rft_dat=%3Cthieme_cross%3E10_1055_s_0039_1690243%3C/thieme_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true