Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives

A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjug...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2015-05, Vol.80 (9), p.4611-4617
Main Authors: Luo, Xiaoyan, Ge, Li-Shi, An, Xing-Lan, Jin, Jing-Hai, Wang, Yu, Sun, Pei-Pei, Deng, Wei-Ping
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Molecular Structure
Stereoisomerism
Thioamides - chemistry
Thiophenes - chemical synthesis
Thiophenes - chemistry
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-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3
cites cdi_FETCH-LOGICAL-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3
container_end_page 4617
container_issue 9
container_start_page 4611
container_title Journal of organic chemistry
container_volume 80
creator Luo, Xiaoyan
Ge, Li-Shi
An, Xing-Lan
Jin, Jing-Hai
Wang, Yu
Sun, Pei-Pei
Deng, Wei-Ping
description A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjugate addition cascade reaction and provides a straightforward synthetic protocol for constructing 2,3,5-trisubstituted 2-aminothiophenes.
doi_str_mv 10.1021/acs.joc.5b00488
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1677892165</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1677892165</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3</originalsourceid><addsrcrecordid>eNp1kE1LwzAch4Mobk7P3qRHQbrlpWmz45hOhYniy00oafuPy2ibmbSDefIr-BX9JGZ0ejOX_-X5PYQHoVOChwRTMpK5Gy5NPuQZxpEQe6hPOMVhPMbRPupjTGnIaMx66Mi5JfaPc36IepQLgQnjffT6CG_aOCghb_QagjtoZBnOLEBwX0P4YJrgaVM3C3DaBUYFs7b2oKllqT-gCOj359ek0rVpFtqsFlBDcAlWr-VW5o7RgZKlg5PdHaCX2dXz9Cac31_fTifzUDLGmjCKJOaMUR4VXHGlGCkEZf6zioxxhhMlpUcop0zQnECcKQ7MD1gSMRHFBRug8867sua9BdeklXY5lKWswbQuJXGSiDElMffoqENza5yzoNKV1ZW0m5TgdJs09UlTnzTdJfWLs528zSoo_vjfhh646IBu2Vofx_2r-wEoxYHt</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1677892165</pqid></control><display><type>article</type><title>Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Luo, Xiaoyan ; Ge, Li-Shi ; An, Xing-Lan ; Jin, Jing-Hai ; Wang, Yu ; Sun, Pei-Pei ; Deng, Wei-Ping</creator><creatorcontrib>Luo, Xiaoyan ; Ge, Li-Shi ; An, Xing-Lan ; Jin, Jing-Hai ; Wang, Yu ; Sun, Pei-Pei ; Deng, Wei-Ping</creatorcontrib><description>A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjugate addition cascade reaction and provides a straightforward synthetic protocol for constructing 2,3,5-trisubstituted 2-aminothiophenes.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b00488</identifier><identifier>PMID: 25880135</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkynes - chemistry ; Molecular Structure ; Stereoisomerism ; Thioamides - chemistry ; Thiophenes - chemical synthesis ; Thiophenes - chemistry</subject><ispartof>Journal of organic chemistry, 2015-05, Vol.80 (9), p.4611-4617</ispartof><rights>Copyright © American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3</citedby><cites>FETCH-LOGICAL-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25880135$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Luo, Xiaoyan</creatorcontrib><creatorcontrib>Ge, Li-Shi</creatorcontrib><creatorcontrib>An, Xing-Lan</creatorcontrib><creatorcontrib>Jin, Jing-Hai</creatorcontrib><creatorcontrib>Wang, Yu</creatorcontrib><creatorcontrib>Sun, Pei-Pei</creatorcontrib><creatorcontrib>Deng, Wei-Ping</creatorcontrib><title>Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjugate addition cascade reaction and provides a straightforward synthetic protocol for constructing 2,3,5-trisubstituted 2-aminothiophenes.</description><subject>Alkynes - chemistry</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><subject>Thioamides - chemistry</subject><subject>Thiophenes - chemical synthesis</subject><subject>Thiophenes - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LwzAch4Mobk7P3qRHQbrlpWmz45hOhYniy00oafuPy2ibmbSDefIr-BX9JGZ0ejOX_-X5PYQHoVOChwRTMpK5Gy5NPuQZxpEQe6hPOMVhPMbRPupjTGnIaMx66Mi5JfaPc36IepQLgQnjffT6CG_aOCghb_QagjtoZBnOLEBwX0P4YJrgaVM3C3DaBUYFs7b2oKllqT-gCOj359ek0rVpFtqsFlBDcAlWr-VW5o7RgZKlg5PdHaCX2dXz9Cac31_fTifzUDLGmjCKJOaMUR4VXHGlGCkEZf6zioxxhhMlpUcop0zQnECcKQ7MD1gSMRHFBRug8867sua9BdeklXY5lKWswbQuJXGSiDElMffoqENza5yzoNKV1ZW0m5TgdJs09UlTnzTdJfWLs528zSoo_vjfhh646IBu2Vofx_2r-wEoxYHt</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Luo, Xiaoyan</creator><creator>Ge, Li-Shi</creator><creator>An, Xing-Lan</creator><creator>Jin, Jing-Hai</creator><creator>Wang, Yu</creator><creator>Sun, Pei-Pei</creator><creator>Deng, Wei-Ping</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150501</creationdate><title>Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives</title><author>Luo, Xiaoyan ; Ge, Li-Shi ; An, Xing-Lan ; Jin, Jing-Hai ; Wang, Yu ; Sun, Pei-Pei ; Deng, Wei-Ping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkynes - chemistry</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><topic>Thioamides - chemistry</topic><topic>Thiophenes - chemical synthesis</topic><topic>Thiophenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luo, Xiaoyan</creatorcontrib><creatorcontrib>Ge, Li-Shi</creatorcontrib><creatorcontrib>An, Xing-Lan</creatorcontrib><creatorcontrib>Jin, Jing-Hai</creatorcontrib><creatorcontrib>Wang, Yu</creatorcontrib><creatorcontrib>Sun, Pei-Pei</creatorcontrib><creatorcontrib>Deng, Wei-Ping</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Luo, Xiaoyan</au><au>Ge, Li-Shi</au><au>An, Xing-Lan</au><au>Jin, Jing-Hai</au><au>Wang, Yu</au><au>Sun, Pei-Pei</au><au>Deng, Wei-Ping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-05-01</date><risdate>2015</risdate><volume>80</volume><issue>9</issue><spage>4611</spage><epage>4617</epage><pages>4611-4617</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A facile metal-free synthesis of 2-aminothiophene derivatives by the reaction of 2-ynals with thioamides in alcohols has been developed. This transformation allows the assembly of 2-aminothienyl ether derivatives via a well-designed aldol condensation/regioselective intramolecular cyclization/conjugate addition cascade reaction and provides a straightforward synthetic protocol for constructing 2,3,5-trisubstituted 2-aminothiophenes.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25880135</pmid><doi>10.1021/acs.joc.5b00488</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2015-05, Vol.80 (9), p.4611-4617
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1677892165
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Alkynes - chemistry
Molecular Structure
Stereoisomerism
Thioamides - chemistry
Thiophenes - chemical synthesis
Thiophenes - chemistry
title Regioselective Metal-Free One-Pot Synthesis of Functionalized 2‑Aminothiophene Derivatives
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-09-21T10%3A46%3A15IST&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=Regioselective%20Metal-Free%20One-Pot%20Synthesis%20of%20Functionalized%202%E2%80%91Aminothiophene%20Derivatives&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Luo,%20Xiaoyan&rft.date=2015-05-01&rft.volume=80&rft.issue=9&rft.spage=4611&rft.epage=4617&rft.pages=4611-4617&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.5b00488&rft_dat=%3Cproquest_cross%3E1677892165%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a333t-44a0533254d5f5ff31d823000f190b07faa44a252382c1e6bf5e35333743846d3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1677892165&rft_id=info:pmid/25880135&rfr_iscdi=true