405064-47-3Relevant academic research and scientific papers
β-Silyl-Assisted Tandem Diels-Alder/Nazarov Reaction of 1-Aryl-3-(trimethylsilyl) Ynones
Carmichael, Rachael A.,Sophanpanichkul, Punyanuch,Chalifoux, Wesley A.
supporting information, p. 2592 - 2595 (2017/05/24)
A one-pot tandem Diels-Alder/Nazarov reaction of 1-aryl-3-(trimethylsilyl) ynones has been achieved to generate carbo- and heterocyclic fused ring systems in good to excellent yields. The β-silyl effect is instrumental in accessing this otherwise challenging cascade annulation reaction. The tandem reaction proceeds in the presence of BCl3 to generate three new carbon-carbon bonds, a quaternary carbon, and two stereogenic centers with excellent diastereocontrol. A variety of substituted arenes, and even heteroaromatics, are tolerated to provide tricyclic products that are of interest as advanced intermediates toward biologically relevant compounds.
Synthesis of 3-carbonyl pyrazole-5-phosphonates via 1,3-dipolar cycloaddition of Bestmann-Ohira reagent with ynones
Pramanik, Mukund M.D.,Kant, Ruchir,Rastogi, Namrata
, p. 5214 - 5220 (2014/07/08)
The present work explores the hitherto unexplored reactivity of ynones as dipolarophiles with Bestmann-Ohira reagent. The reaction offers a convenient route for the synthesis of regioisomerically pure 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles in
Synthesis of 3-carbonyl pyrazole-5-phosphonates via 1,3-dipolar cycloaddition of Bestmann-Ohira reagent with ynones
Pramanik, Mukund M.D.,Kant, Ruchir,Rastogi, Namrata
, p. 5214 - 5220 (2014/12/10)
The present work explores the hitherto unexplored reactivity of ynones as dipolarophiles with Bestmann-Ohira reagent. The reaction offers a convenient route for the synthesis of regioisomerically pure 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles in
Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements
Shi Shun, Annabelle L. K.,Chernick, Erin T.,Eisler, Sara,Tykwinski, Rik R.
, p. 1339 - 1347 (2007/10/03)
Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis.
InBr3-Catalyzed Alkynylation and Allylation of Acid Chlorides: A Facile Synthesis of Alkynyl and Allyl Ketones
Yadav,Reddy,Reddy, M. Sridhar,Parimala
, p. 2390 - 2394 (2007/10/03)
Alkynylsilanes and allyltrimethylsilane undergo smooth coupling with acid chlorides in the presence of 5 mol% of indium tribromide under mild conditions to afford the corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in excellent yields in a short reaction time with high selectivity.
Elemental iodine-catalyzed coupling of alkynylsilanes with acid chlorides: A facile synthesis of α,β-acetylenic ketones
Yadav,Reddy,Reddy, M. Sridhar
, p. 1722 - 1724 (2007/10/03)
Alkynylsilanes undergo coupling smoothly with acid chlorides in the presence of molecular iodine under mild reaction conditions to afford the corresponding α, β-acetylenic ketones in excellent yields in a short reaction time with high selectivity.
Modification of the Fritsch-Buttenberg-Wiechell rearrangement: A facile route to unsymmetrical butadiynes
Chernick, Erin T,Eisler, Sara,Tykwinski, Rik R
, p. 8575 - 8578 (2007/10/03)
A modification of the Fritsch-Buttenberg-Wiechell rearrangement has been used to form unsymmetrically substituted 1,3-butadiynes from 1,1-dibromo-olefin precursors. The reaction proceeds via lithium-halogen exchange, followed by migration of the aryl or alkynyl moiety to provide the butadiyne framework. The facile formation of the dibromo-olefins in three steps from commercially available aryl aldehydes or carboxylic acid chlorides makes this procedure an attractive alternative to traditional methods for butadiyne synthesis.
