2219-66-1Relevant articles and documents
A new pd-catalyzed cascade reaction for the synthesis of strained aromatic polycycles
Blond, Gaelle,Bour, Christophe,Salem, Bahaa,Suffert, Jean
, p. 1075 - 1078 (2008)
Two new palladium catalyzed cascade reactions involving a 4-exo-dig cyclocarbopalladation are described. These processes are shown to convert bromoenediynes and bromodienynes into strained aromatic compounds in a single step.
The Aza Diels-Alder Reaction on Brominated Conjugated Dienes
Navarro, Jorge A. R.,Oltra, J. Enrique,Roldan-Molina, Esther,Uceda, Rafael G.
supporting information, p. 2003 - 2005 (2021/06/25)
The use of electron-deficient dienes as substrates in the aza Diels-Alder reaction (ADA) has been studied scarcely. However, the ADA process offers a wide range of applications in organic synthesis. In this communication, the reaction between different brominated conjugated dienes and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), one of the most vigorous dienophiles, is reported. We have synthesized tricyclic compounds from acyclic substrates in only two steps, considering variables such as ring size and steric hindrance and substantially improved the results obtained with other dienophiles.
1,2-Dibromotetrachloroethane: An efficient reagent for many transformations by modified Appel reaction
Essiz, Sel?uk,Da?tan, Arif
, p. 150 - 156 (2019/05/16)
An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcohols under mild conditions using a triphenylphosphine (PPh 3) /1,2-dibromotetrachloroethane (DBTCE) complex in excellent yields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to their corresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied to ring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydrides under very mild experimental conditions are also successfully accomplished by following a modification of the Appel reaction protocol in this work.
When cobalt-mediated [2 + 2 + 2] cycloaddition reaction dares go astray: Synthesis of unprecedented cobalt(III)-complexes
Delorme, Marion,Punter, Alexander,Oliveira, Raquel,Aubert, Corinne,Carissan, Yannick,Parrain, Jean-Luc,Amatore, Muriel,Nava, Paola,Commeiras, Laurent
supporting information, p. 15767 - 15771 (2019/11/11)
In sharp contrast with the standard [2 + 2 + 2] cycloaddition reaction of diyne/ene, cobalt-mediated cycloadditions with γ-alkylidenebutenolide led to unprecedented cobalt(iii) polycyclic complexes. A plausible mechanism supported by a computational study based on an unusual fragmentation of the butenolide moiety was postulated to account for this original reaction.
A new synthetic route for the synthesis of enantioenriched 1,2,3,4-tetrahydronaphthalene-derived 1,3-diols
Cheng, Feng,Cai, Chen,Yang, Xing,Lin, Zi-Wei,Hu, Xiao-Song,Huang, Yi-Yong
, p. 2859 - 2865 (2018/12/04)
In this report, we presented a new approach to access a (1,3-butadiene-2-yl)carbinol, (1R,2R)- and (1S,2S)-1-(hydroxymethyl)-1-vinyl-1,2,3,4-tetrahydronaphthalene-2-ols. Starting from commercially available 1,4-diol-2-butyne, a six-step synthesis involving dibromination, Zn-mediated addition reaction of phenylpropyl aldehyde, epoxidation, epoxy–arene cyclization, and resolution with D(+)-Camphor afforded the title compounds.
Increasing the efficiency of the transannular diels-alder strategy via palladium(II)-catalyzed macrocyclizations
Iafe, Robert G.,Kuo, Jonathan L.,Hochstatter, Dustin G.,Saga, Tomomi,Turner, Jonathan W.,Merlic, Craig A.
supporting information, p. 582 - 585 (2013/04/10)
Palladium(II)-catalyzed macrocyclizations of bis(vinylboronate ester) compounds are demonstrated to provide a strategically efficient approach to transannular Diels-Alder reaction substrates. In several systems reported, the macrocycle is preorganized such that cycloaddition at room temperature occurs concomitantly with cyclization. Numerous advantages over palladium(0)-catalyzed cross-coupling approaches are demonstrated.
Hybrids of sugars and aromatics: A Pd-catalyzed modular approach to chromans and isochromans
Leibeling, Markus,Koester, Dennis C.,Pawliczek, Martin,Kratzert, Daniel,Dittrich, Birger,Werz, Daniel B.
scheme or table, p. 3656 - 3667 (2010/08/05)
Herein we describe the synthesis of highly substituted chromans and isochromans using carbohydrates as starting materials. The key step of our synthetic approach is the annelation of the benzene moiety via a highly efficient Pd-catalyzed domino reaction. This powerful approach led to a small library of highly substituted chromans and isochromans by making use of a variety of different diynes and bromoglycals. We investigated several Pd-catalysts in order to improve the yields and to enlarge the scope of the domino reaction. Furthermore, we elucidated the mechanistic picture of the reaction with isotope-labelling experiments. Most probably the reaction proceeds via an oxidative addition followed by two carbopalladation steps and a final cyclization reaction.
Air-stable {(C5H5)Co} catalysts for [2+2+2] cycloadditions
Geny, Anais,Agenet, Nicolas,Iannazzo, Laura,Malacria, Max,Aubert, Corinne,Gandon, Vincent
supporting information; body text, p. 1810 - 1813 (2009/09/05)
Cobalt cyclopentadienyl complexes incorporating a fumarate and a CO ligand (see picture) efficiently catalyze inter-and intramolecular [2+2+2] cycloadditions of alkynes, nitriles, and/or alkenes to give benzenes, pyridines, or 1,3-cyclohexadienes. Unlike catalysts such as [CpCo (CO)2] or [CpCo(C2H4)2] (Cp=C5H5), they are air-stable, easy to handle, compatible with microwave conditions, and do not necessarily require irradiation to be active.
Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 2: Structure-activity relationships for substituted 2-aryl-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-(piperidin-1-yl)butanes
Finke, Paul E.,Meurer, Laura C.,Oates, Bryan,Mills, Sander G.,MacCoss, Malcolm,Malkowitz, Lorraine,Springer, Martin S.,Daugherty, Bruce L.,Gould, Sandra L.,DeMartino, Julie A.,Siciliano, Salvatore J.,Carella, Anthony,Carver, Gwen,Holmes, Karen,Danzeisen, Renee,Hazuda, Daria,Kessler, Joseph,Lineberger, Janet,Miller, Michael,Schleif, William A.,Emini, Emilio A.
, p. 265 - 270 (2007/10/03)
(2S)-2-(3,4-Dichlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[spiro(2 ,3-dihydrobenzthiophene-3,4′-piperidin-1′yl)]butane S-oxide (3) has been identified as a potent CCR5 antagonist lead structure having an IC50 = 35 nM. Herein, we describe the structure-activity relationship studies directed toward the requirement for and optimization of the C-2 phenyl fragment. The phenyl was found to be important for CCR5 antagonism and substitution was limited to small moieties at the 3-position (13 and 16: X = H, 3-F, 3-Cl, 3-Me).
A short survey of bycyclic diamines-syntheses and properties of N,N′-bridged-1,10-diazabicyclooctadeca-5,14-diynes
Von Hirschheydt, Thomas,Wolfart, Volker,Gleiter, Rolf,Irngartinger, Hermann,Oeser, Thomas,Rominger, Frank,Eisentraeger, Frank
, p. 175 - 183 (2007/10/03)
The conformations and properties of 1,(k + 2)-diazabicyclo[k.l.m]alkanes are reviewed briefly. In these species the alkane chains allow inside protonation but no metal complexation. Inside metal complexation is made possible if the alkane chains incorporate alkyne units. The preparation and structures of bridged 1,10-diazacyclooctadeca-5,14-diynes are reported. As bridges we use simple alkyl chains from (CH2)2 to (Ch2)10, di- and triethyleneglycol, but-2-yne, hex-3-yne, and oct-4-yne chains. The resulting bicyclic systems, 34-47, adopt in the solid state either the in/in or the out/out conformations. By means of dynamic NMR spectroscopy a homeomorphic isomerism in 34 was uncovered. A second dynamic process, a "wagging" motion of the alkyne bridges, could be studied in case of 35. The molecular dimensions in the solid state reveal N ... N distances between 3.16 A and 6.52 A. The intramolecular distances between the triple bonds vary between 4.25 A and 7.31 A.
