2216-94-6Relevant articles and documents
On the synthesis of arylpropiolic acids and investigations towards the formation of vinyl chlorides by HCl addition during esterification reactions
Hapke, Marko,Kral, Karolin,Spannenberg, Anke
, p. 642 - 652 (2011)
The synthesis protocol for the preparation of different arylpropiolic acids using the Negishi reaction and the addition of HCl to the alkyne moiety of these acids in subsequent esterification reactions using SOCl2 was examined. Georg Thieme Verlag Stuttgart New York.
Facile Dehydration of Activated Ketones to Alkynes
Hendrickson, James B.,Hussoin, Md. Sajjat
, p. 217 - 218 (1989)
Ketones activated by β-carbonyl or phenyl groups are readily dehydrated to alkynes with (PhP(1+))2O, 2OTf(1-) and triethylamine in refluxing 1,2-dichloroethane.
Palladium-catalyzed coupling of alkynes with chloroformates to form alkynecarboxylic acid esters
Boettcher, Arnd,Becker, Heike,Brunner, Melanie,Preiss, Thomas,Henkelmann, Jochem,De Bakker, Christel,Gleiter, Rolf
, p. 3555 - 3556 (1999)
The preparation of alkynecarboxylic acid esters, which are versatile building blocks for the synthesis of heterocyclic compounds, is described by means of the, palladium-catalyzed coupling of alkynes with chloroformates for the first time. The Royal Society of Chemistry 1999.
Skeletally Tunable Seven-Membered-Ring Fused Pyrroles
Andreou, Dimitrios,Essien, Nsikak B.,Pubill-Ulldemolins, Cristina,Terzidis, Michael A.,Papadopoulos, Athanasios N.,Kostakis, George E.,Lykakis, Ioannis N.
supporting information, p. 6685 - 6690 (2021/09/11)
We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.
Ball-Milling-Enabled Reactivity of Manganese Metal**
Bolt, Robert R. A.,Browne, Duncan L.,Howard, Joseph L.,Khan, Adam,Magri, Giuseppina,Morrill, Louis C.,Nicholson, William I.,Richards, Emma,Seastram, Alex C.
supporting information, p. 23128 - 23133 (2021/09/20)
Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.
Selective synthesis of trisubstituted pyrroles through the reactions of alkynyl Fischer carbene complexes with oxazolones
López, Julio,Velazco-Cabral, Iván,Rodríguez-DeLeón, Eloy,Villegas Gómez, Clarisa,Delgado, Francisco,Tamariz, Joaquín,Arrieta, Ana,Cossío, Fernando P.,Vázquez, Miguel A.
supporting information, p. 538 - 550 (2020/01/30)
An efficient and simple synthesis of novel trisubstituted 1H-pyrroles 4a-qvia 1,3-dipolar cycloaddition of Δ3-trifluoromethyloxazolones 2a-d with both chromium and tungsten alkynyl Fischer carbene complexes (1a-h) is described. An unexpected and unreported -CF3 group elimination process was observed in the pyrrole structure. Our experimental and theoretical data suggested that the metal fragment may be responsible for this phenomenon. The dipolar cycloaddition proceeded efficiently to produce a single regioisomer, which was unambiguously established through NMR and single-crystal X-ray diffraction studies. Nevertheless, the reaction of alkynyl carbenes bearing an α,β,γ,δ-unsaturated moiety with excess oxazolone 2a produced a polycyclic compound 6 speculatively formed through a cascade reaction involving 1,6-, 1,4- and 1,2-nucleophilic addition steps.