Synthesis of dispirocyclopentyl-3,3′-bisoxindoles via base promoted cyclization reaction of 3-phenacylideneoxindoles with nitromethane

A special kind of dispirocyclopentyl-3,3′-bisoxindoles, in which the two oxindole units exist at 1,2-positions of the newly formed cyclopentyl ring, were conveniently prepared in 49–86% yields by cyclization reaction of nitromethane with two molecules of 3-phenacylideneoxindoles in refluxing ethanol...

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Veröffentlicht in:	Tetrahedron 2014-12, Vol.70 (51), p.9587-9591
Hauptverfasser:	Lu, Li-Juan, Yan, Chao-Guo
Format:	Artikel
Sprache:	eng
Schlagworte:	Cycloaddition Diastereoselectivity Dispirocyclopentyl-3,3′-bisoxindole Ethanol Ethyl alcohol Nitromethane Refluxing Spirooxindole Synthesis (chemistry) Tetrahedrons
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creator	Lu, Li-Juan Yan, Chao-Guo
description	A special kind of dispirocyclopentyl-3,3′-bisoxindoles, in which the two oxindole units exist at 1,2-positions of the newly formed cyclopentyl ring, were conveniently prepared in 49–86% yields by cyclization reaction of nitromethane with two molecules of 3-phenacylideneoxindoles in refluxing ethanol in the presence of DBU as base. The reaction has the advantages of readily available starting materials, operational simplicity, good yields, and high diastereoselectivity. [Display omitted]
doi_str_mv	10.1016/j.tet.2014.11.028
format	Article
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The reaction has the advantages of readily available starting materials, operational simplicity, good yields, and high diastereoselectivity. 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The reaction has the advantages of readily available starting materials, operational simplicity, good yields, and high diastereoselectivity. [Display omitted]</description><subject>Cycloaddition</subject><subject>Diastereoselectivity</subject><subject>Dispirocyclopentyl-3,3′-bisoxindole</subject><subject>Ethanol</subject><subject>Ethyl alcohol</subject><subject>Nitromethane</subject><subject>Refluxing</subject><subject>Spirooxindole</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kLGO1DAQhi0EEsvBA9ClpCA5T-zEiajQiYOTTqIAasuxJ9pZZe1g-w5CRcnz8Eg8CV4WiY5qppjv1z8fY8-BN8Chvzw0GXPTcpANQMPb4QHbgexl3UnoH7Id55LXkrf8MXuS0oFzDtCKHfvxYfN5j4lSFebKUVopBrvZJazo87bU4qX49f1nPVEKX8m7sGCq7slUk0lYrTEcQ0ZXnQj6ZjIFX0U09s9SAkW97tEbuy3k0OO_iC-U95WnXAIw743Hp-zRbJaEz_7OC_bp-s3Hq3f17fu3N1evb2vbyi7X0qhRcT73I06DUwblhGYYe2dlOyG4dhSohFBcdThM0HWjG5UdAIe5t1M_iQv24pxbun--w5T1kZLFZSkdwl3SoKTs1Sg6VU7hfGpjSCnirNdIRxM3DVyfrOuDLtb1yboG0MV6YV6dGSw_3BNGnSyht-goos3aBfoP_RswXY-5</recordid><startdate>20141223</startdate><enddate>20141223</enddate><creator>Lu, Li-Juan</creator><creator>Yan, Chao-Guo</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20141223</creationdate><title>Synthesis of dispirocyclopentyl-3,3′-bisoxindoles via base promoted cyclization reaction of 3-phenacylideneoxindoles with nitromethane</title><author>Lu, Li-Juan ; Yan, Chao-Guo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c245t-4a79700f69eb8d7ae4bea896dc42be1d293e7337075e8b1559d97c81e8f6cb6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Cycloaddition</topic><topic>Diastereoselectivity</topic><topic>Dispirocyclopentyl-3,3′-bisoxindole</topic><topic>Ethanol</topic><topic>Ethyl alcohol</topic><topic>Nitromethane</topic><topic>Refluxing</topic><topic>Spirooxindole</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lu, Li-Juan</creatorcontrib><creatorcontrib>Yan, Chao-Guo</creatorcontrib><collection>CrossRef</collection><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>Lu, Li-Juan</au><au>Yan, Chao-Guo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of dispirocyclopentyl-3,3′-bisoxindoles via base promoted cyclization reaction of 3-phenacylideneoxindoles with nitromethane</atitle><jtitle>Tetrahedron</jtitle><date>2014-12-23</date><risdate>2014</risdate><volume>70</volume><issue>51</issue><spage>9587</spage><epage>9591</epage><pages>9587-9591</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A special kind of dispirocyclopentyl-3,3′-bisoxindoles, in which the two oxindole units exist at 1,2-positions of the newly formed cyclopentyl ring, were conveniently prepared in 49–86% yields by cyclization reaction of nitromethane with two molecules of 3-phenacylideneoxindoles in refluxing ethanol in the presence of DBU as base. 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subjects	Cycloaddition Diastereoselectivity Dispirocyclopentyl-3,3′-bisoxindole Ethanol Ethyl alcohol Nitromethane Refluxing Spirooxindole Synthesis (chemistry) Tetrahedrons
title	Synthesis of dispirocyclopentyl-3,3′-bisoxindoles via base promoted cyclization reaction of 3-phenacylideneoxindoles with nitromethane
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