Gold(I)‐Catalyzed Carbothiolation via Rearrangement of S‐Propargyl Group: An Access to 3‐Allenyl or 3‐Indenyl Benzo[b]thiophenes
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Abstract A series of 3‐allenyl benzo[b]thiophenes were synthesized through a gold(I)‐catalyzed domino reaction. The process consists in a 5‐ endo ‐dig cyclization with C−S bond formation and consecutive S‐to‐C propargyl migration via [3,3]‐sigmatropic Claisen rearrangement. With aryl substituents on both triple bonds of the substrate, subsequent intramolecular hydroarylation on the formed allenyl system led to 3‐indenyl benzo[b]thiophenes. From a substrate bearing a 3‐butynol moiety diverse fused O ‐heterocycles have been obtained via intramolecular hydroalkoxylation. A gold‐mediated 1,3‐migration involving allenyl to propargyl rearrangement is also described. magnified imageKeywords:
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Domino
[reaction: see text] 1,6-Enynes and allyl propargyl ethers undergo a cobalt-catalyzed formal 5-endo-dig cyclization to form vinyl cyclopentenes and dihydrofurans, respectively. The use of equimolar amounts of dicobalt octacarbonyl and trimethyl phosphite affords optimum yields and improved selectivity for cycloisomerization vs alkene isomerization.
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Thio-Claisen rearrangement of a number of 3-(4-aryloxybut-2 – ynlthio)benzofurans has been achieved under very mild conditions to give 2H-benzo[b]thiopyrano[2,3-d]furans. Attempts at further thio-claisen rearrangement resulted in the occurrence of thermal [1s, 3a] sigmatropic shift. Keywords: Thio-Claisen rearrangement, [3,3] sigmatropic rearrangement, sulfur heterocycles, regioselective cyclization, [1,3] hydrogen shift, thiopyrano, thieno[3,2-c]coumarins, methyl, pyranothiopyran, furan
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Allyl propargyl ethers undergo cobalt-mediated cycloisomerization reactions to form dihydrofurans in good yield and with excellent diastereoselectivity. The reaction works with a range of substrates, and its utility in synthesis is exemplified by the preparation of a bistetrahydrofuran unit.
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Starting from propargyl sulfonamides and 2-bromoallenes an efficient preparation of N-propargyl-N-vinyl sulfonamides is developed.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Abstract For Abstract see ChemInform Abstract in Full Text.
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ADVERTISEMENT RETURN TO ISSUEPREVLetterNEXTA Practical Method for Oxazole Synthesis by Cycloisomerization of Propargyl AmidesPeter Wipf, Yasunori Aoyama, and Tyler E. BenedumView Author Information Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 Cite this: Org. Lett. 2004, 6, 20, 3593–3595Publication Date (Web):August 28, 2004Publication History Received29 July 2004Published online28 August 2004Published inissue 1 September 2004https://pubs.acs.org/doi/10.1021/ol0485058https://doi.org/10.1021/ol0485058rapid-communicationACS PublicationsCopyright © 2004 American Chemical SocietyRequest reuse permissionsArticle Views4977Altmetric-Citations101LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Amides,Isomerization,Ketones,Organic compounds,Silica Get e-Alerts
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
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Abstract For Abstract see ChemInform Abstract in Full Text.
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The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.
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