Journal ArticleDOI
Synthesis of dichloromethyl-substituted salicylates and pyran-4-ones by cyclocondensation of 1,3-bis(silyloxy)-1,3-butadienes with 1,1-dimethoxy-4,4-dichlorobut-1-en-3-one: control of the C,C- and C,O-regioselectivity by the choice of Lewis acid
Vahuni Karapetyan,Satenik Mkrtchyan,Gagik Ghazaryan,Alexander Villinger,Christine Fischer,Peter Langer +5 more
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TLDR
The use of Me3SiOTf instead of TiCl4 resulted in a change of the regioselectivity and in the formation of functionalized 2-(dichloromethyl)pyran-4-ones.About:
This article is published in Tetrahedron.The article was published on 2009-11-07. It has received 8 citations till now. The article focuses on the topics: Regioselectivity & Lewis acids and bases.read more
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Cobalt-catalyzed 1,4-hydrovinylation of allylsilane and allylboronic esters for the synthesis of hydroxy-functionalized 1,4-dienes.
TL;DR: Polyfunctionalized complex structures can be generated by both approaches in a convergent fashion.
Journal ArticleDOI
Six-Membered Ring Systems: With O and/or S Atoms
John D. Hepworth,B. Mark Heron +1 more
TL;DR: In this article, a review of reaction chemistry and new ring synthetic methods for pyranones is presented, which covers work published in the calendar year 2010 and includes new ring synthesis methods for trioxanes, tetraoxane, dioxanes, trithianes and oxathianes.
Journal ArticleDOI
Formal [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 1-chloro-1,1-difluoro-4,4-dimethoxybut-3-en-2-one and 1,1-difluoro-4,4-dimethoxybut-3-en-2-one. Regioselective synthesis of fluorinated salicylates and pyran-4-ones
Sebastian Reimann,Alina Bunescu,Robert Litschko,Silke Erfle,Lutz Domke,Franziska Bendrath,Zharylkasyn A. Abilov,Anke Spannenberg,Alexander Villinger,Peter Langer +9 more
TL;DR: In this article, the Me3SiOTf-mediated cyclocondensation of the same building blocks provided CF2Cl- and CF2H-substituted pyran-4-ones, while the cyclization of C4-addienes with 1,1-difluoro-4,4-dimethoxybut-3-en-2-one failed.
Journal ArticleDOI
Identification of reaction intermediates in AlCl3-mediated cyclocondensation reactions by simultaneous in situ ATR-FTIR and UV–vis spectroscopy
Sebastian Reimann,Leif R. Knöpke,Anke Spannenberg,Angelika Brückner,Oliver Kühn,Peter Langer,Ursula Bentrup +6 more
TL;DR: In this article, a functionalized trifluoromethyl-substituted salicylates have been synthesized based on AlCl3-mediated cyclocondensation reactions using 4,4-dimethoxy-1, 1,1-trifluorsobut-3-en-2-one and 1,3-bis(silyloxy)-1, 3-butadienes.
References
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Journal ArticleDOI
Chemistry of enol silyl ethers. 5. A novel cycloaromatization reaction. Regiocontrolled synthesis of substituted methyl salicylates
Tak Hang Chan,Peter Brownbridge +1 more
Journal ArticleDOI
Cyclization reactions of 1,3-bis-silyl enol ethers and related masked dianions
TL;DR: In this article, the use of 1,3-bis-silyl enol ethers, electroneutral 1, 3-dicarbonyl dianion equivalents, in Lewis acid catalyzed reactions was proposed.
Journal ArticleDOI
Neighboring group participation in Lewis acid-promoted [3 + 4] and [3 + 5] annulations. The synthesis of oxabicyclo[3.n.1]alkan-3-ones
TL;DR: In this article, Lewis acids are employed as catalysts in the annulation of 1,4 and 1,5-dicarbonyl dielectrophiles with bis(trimethylsilyl) enol ethers of β-diketones and β-keto esters.
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Chemistry of enol silyl ethers. A general synthesis of 3-hydroxyhomophthalates and a biomimetic synthesis of sclerin
TL;DR: A general synthesis of 3-hydroxy homophthalates was developed and applied to the synthesis of sclerin (24), a compound possessing plant-growth activity.
Journal ArticleDOI
Preparation of triazolo[1,5-c]pyrimidines as potential antiasthma agents
J. B. Medwid,Rolf Paul,J. S. Baker,Brockman Ja,M. T. Du,W. A. Hallett,J. W. Hanifin,Robert A. Hardy,M. E. Tarrant,L. W. Torley +9 more
TL;DR: Five compounds prepared by reacting arylamidines with sodium ethyl formylacetate or with ethyl propiolate to give pyrimidinones were found to have the best activity and were chosen for further pharmacological and toxicological study.