17950-66-2Relevant academic research and scientific papers
Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines
Dohe, Janis,Müller, Thomas J. J.
, p. 705 - 718 (2016/07/06)
The concatenation of the modified Sonogashira alkynone synthesis and the Bagley-Bohlmann-Rahtz pyridine synthesis gives novel consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz (cBBR) syntheses of tri- and tetrasubstituted pyridines in a one-pot fashion. With these processes 15 differently substituted 3-ethoxycarbonyl 2-methylpyridines can be readily obtained in modest to moderate yields.
Synthesis of ynones via recyclable polystyrene-supported palladium(0) complex catalyzed acylation of terminal alkynes with acyl chlorides under copper- and solvent-free conditions
Bakherad, Mohammad,Keivanloo, Ali,Bahramian, Bahram,Jajarmi, Saeideh
experimental part, p. 311 - 314 (2011/04/12)
Herein, a highly efficient method for the copper- and solvent-free coupling reaction of acyl chlorides and terminal alkynes catalyzed by 1-phenyl-1,2-propanedione-2-oxime thiosemicarbazone-functionalized polystyrene resin-supported Pd(0) complex is descri
One-pot three-step synthesis of 1,2,3-triazoles by copper-catalyzed cycloaddition of azides with alkynes formed by a Sonogashira cross-coupling and desilylation
Friscourt, Frederic,Boons, Geert-Jan
supporting information; experimental part, p. 4936 - 4939 (2010/12/25)
A microwave-assisted, one-pot, three-step Sonogashira cross-coupling- desilylation-cycloaddition sequence was developed for the convenient preparation of 1,4-disubstituted 1,2,3-triazoles starting from a range of halides, acyl chlorides, ethynyltrimethyls
New Entry to a Three-Component Pyrimidine Synthesis by TMS-Ynones via Sonogashira Coupling
Karpov, Alexei S.,Mueller, Thomas J. J.
, p. 3451 - 3454 (2007/10/03)
(Equation presented) TMS-ynones are versatile synthetic equivalents of β-keto aldehydes and can be readily synthesized in an atom-economical fashion by coupling (het)aroyl chlorides and (TMS)-acetylene with only one equiv (!) of triethylamine under Sonogashira conditions. This mild ynone synthesis is also a suitable entry to 2,4-disubstituted pyrimidines in the sense of a one-pot three-component reaction, i.e., a coupling-addition- cyclocondensation sequence.
Palladium-Catalyzed Reactions of Acyl Chlorides with (1-Alkynyl)tributylstannanes. A Convenient Synthesis for 1-Alkynyl Ketones
Logue, Marshall W.,Teng, Kelly
, p. 2549 - 2553 (2007/10/02)
Acyl chlorides couple with (1-alkynyl)tributylstannanes in the presence of catalytic amounts of palladium(II) or palladium(0) complexes to produce 1-alkynyl ketones in respectable yields.The couplings of isobutyryl, acetyl, benzoyl, and p-nitrobenzoyl chlorides with phenylethynyl-, (trimethylsilyl)ethynyl-, (carbomethoxy)ethynyl-, -1-propynyl>-, and (3,3-diethoxy-1-propynyl)tributylstannanes were investigated in the presence of tetrakis(triphenylphosphine)palladium(O), benzylchlorobis(triphenylphosphine)palladium(II), dichlorobis(triphenylphosphine)palladium(II), or phenyliodobis(triphenylphosphine)palladium(II).The reactions are highly selective in that only the alkynyl groups are transferred from the stannane.
Friedel-crafts reactions of bis(trimethylsilyl)polyynes with acyl chlorides; a useful route to terminal-alkynyl ketones
Walton,Waugh
, p. 45 - 56 (2007/10/05)
Bis(trimethylsilyl)acetylenes, Me3Si(CC)nSiMe3, react with acyl chloride-aluminium chloride complexes, XC6H4 COCl·AlCl3 in methylene chloride at 0-20° to form the corresponding ketones XC6H4CO(CC)nSiMe3 in excellent (n = 1) or moderate (n = 2, 4) yield. Treatment of the products with aqueous methanolic borax results in virtually quantitative liberation of the terminal alkynyl ketones XC6H4CO(CC)nH. The method provides the first practical route to the ketotetraynes (n = 4) and usefully supplements existing oxidative methods for keto-monoyne and -diyne synthesis. The oxalyl chloride-aluminium chloride complex reacts with Me3SiCCSiMe3 to give the novel silyl-substituted heterocycle (I): {A figure is presented}.
