Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support
A parallel solid-phase synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives was developed. The polymer-supported synthetic route progressed using the sulfide linker via a traceless strategy. The initial synthesis utilized the Thorpe–Ziegler type cyclization of α-haloketone and poly...
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| Veröffentlicht in: | Tetrahedron 2014-12, Vol.70 (48), p.9183-9190 |
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| container_title | Tetrahedron |
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| creator | Lee, Suyoun Lee, Doohyun Song, Kyung-Sik Liu, Kwang-Hyeon Gong, Young-Dae Lee, Taeho |
| description | A parallel solid-phase synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives was developed. The polymer-supported synthetic route progressed using the sulfide linker via a traceless strategy. The initial synthesis utilized the Thorpe–Ziegler type cyclization of α-haloketone and polymer-supported 2,2-dicyanoethene-1,1-bis(thiolate), which was derived from the Merrifield resin. The resulting thiophene resin was introduced to one substitution by N-arylation. After oxidation of sulfides to sulfones in the thiophene resins for subsequent cleavage, nucleophilic desulfonative substitution with amines and thiols afforded the desired thiophene-3-carbonitrile derivatives in good overall yields.
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| doi_str_mv | 10.1016/j.tet.2014.10.030 |
| format | Article |
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[Display omitted]</description><subject>Cleavage</subject><subject>Combinatorial chemistry</subject><subject>Derivatives</subject><subject>Heterocycles</subject><subject>Polymers</subject><subject>Solid-phase synthesis</subject><subject>Strategy</subject><subject>Sulfides</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><subject>Thiophene resins</subject><subject>Thiophene-3-carbonitrile</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWKs_wNsePbh1spvNtngS8QsKetBzyCYTmrLdrJlswX9vSj1LDkOG9xlmHsauOSw4cHm3XSRMiwq4yP8F1HDCZlxIUTaCy1M2AxBQCqjgnF0QbQGA86qese2HjrrvsS_oZ0gbJE9FcEV1K26bMkVPU0fJpymhLdLGh3GDA5Z1aXTswuBzosfCYvR7nfweMzwUKWqDPRIVFHpvC5rGMcR0yc6c7gmv_uqcfT0_fT6-luv3l7fHh3VpBEAqnWhd42qpLV_Wy5VDKyVWKwuytq7rKi60axF4ZxGqFlemBdusdN0sG-TStPWc3RznjjF8T0hJ7TzlhXo9YJhI8VYIucxP5ig_Rk0MRBGdGqPf6fijOKiDV7VV2as6eD20stfM3B8ZzDfsPUZFxuNg0PqIJikb_D_0Lx5vgnc</recordid><startdate>20141202</startdate><enddate>20141202</enddate><creator>Lee, Suyoun</creator><creator>Lee, Doohyun</creator><creator>Song, Kyung-Sik</creator><creator>Liu, Kwang-Hyeon</creator><creator>Gong, Young-Dae</creator><creator>Lee, Taeho</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20141202</creationdate><title>Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support</title><author>Lee, Suyoun ; Lee, Doohyun ; Song, Kyung-Sik ; Liu, Kwang-Hyeon ; Gong, Young-Dae ; Lee, Taeho</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c400t-f47f5f36ad18389fed66e29d063dfbb214af7e01bde027e9c70d59a3585e16c73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Cleavage</topic><topic>Combinatorial chemistry</topic><topic>Derivatives</topic><topic>Heterocycles</topic><topic>Polymers</topic><topic>Solid-phase synthesis</topic><topic>Strategy</topic><topic>Sulfides</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><topic>Thiophene resins</topic><topic>Thiophene-3-carbonitrile</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Suyoun</creatorcontrib><creatorcontrib>Lee, Doohyun</creatorcontrib><creatorcontrib>Song, Kyung-Sik</creatorcontrib><creatorcontrib>Liu, Kwang-Hyeon</creatorcontrib><creatorcontrib>Gong, Young-Dae</creatorcontrib><creatorcontrib>Lee, Taeho</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>Lee, Suyoun</au><au>Lee, Doohyun</au><au>Song, Kyung-Sik</au><au>Liu, Kwang-Hyeon</au><au>Gong, Young-Dae</au><au>Lee, Taeho</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support</atitle><jtitle>Tetrahedron</jtitle><date>2014-12-02</date><risdate>2014</risdate><volume>70</volume><issue>48</issue><spage>9183</spage><epage>9190</epage><pages>9183-9190</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A parallel solid-phase synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives was developed. The polymer-supported synthetic route progressed using the sulfide linker via a traceless strategy. The initial synthesis utilized the Thorpe–Ziegler type cyclization of α-haloketone and polymer-supported 2,2-dicyanoethene-1,1-bis(thiolate), which was derived from the Merrifield resin. The resulting thiophene resin was introduced to one substitution by N-arylation. After oxidation of sulfides to sulfones in the thiophene resins for subsequent cleavage, nucleophilic desulfonative substitution with amines and thiols afforded the desired thiophene-3-carbonitrile derivatives in good overall yields.
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| ispartof | Tetrahedron, 2014-12, Vol.70 (48), p.9183-9190 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Cleavage Combinatorial chemistry Derivatives Heterocycles Polymers Solid-phase synthesis Strategy Sulfides Synthesis (chemistry) Tetrahedrons Thiophene resins Thiophene-3-carbonitrile |
| title | Parallel synthesis of 2,4,5-trisubstituted thiophene-3-carbonitrile derivatives on traceless solid support |
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