A Highly Chemo- and Regioselective N-Acylative Alkynylation of Quinolines with Alkynylsilanes Promoted by Triflate Ion

Yamaguchi, Ryohei; Omoto, Yoshikazu; Miyake, Masaaki; Fujita, Ken‐ichi

doi:10.1246/cl.1998.547

Cited by 23 publications

(5 citation statements)

References 12 publications

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“…They observed that upon N-acylation of quinoline, a stoichiometric amount of silver triflate in refluxing 1,2dichloroethane promotes alkynylation with 1-trimethylsilyl-1alkynes in good yields (Scheme 10). 28 Although no explanation is provided, it seems that alkynyl silvers are formed in such conditions (see sections 5.2, 5.3 and 5.5) and that they add to the N-acylquinolinium formed in situ.…”

Section: Additions To Carbonyl Compounds and Related Compoundsmentioning

confidence: 99%

The organic chemistry of silver acetylides

2007

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Section: Additions To Carbonyl Compounds and Related Compoundsmentioning

confidence: 99%

The organic chemistry of silver acetylides

2007

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“…However, in all cases it was found that the formation of the intermediate pyridinium chloride salt was thermodynamically unfavorable, with the reaction equilibrium largely favoring the two starting materials. To overcome this, a stoichiometric amount of NaOTf was added to increase conversion to the pyridinium salt by the precipitation of NaCl . Reagents 2a and 2b reacted with pyridine in nearly quantitative yields under mild conditions.…”

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confidence: 99%

A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines

Fier

2017

J. Am. Chem. Soc.

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Herein is reported the design and application of a reagent for the direct functionalization of pyridines. These reactions occur under mild conditions and exhibit broad functional group tolerance, enabling the late-stage functionalization of drug-like molecules. The reagent can be easily prepared on large scale from inexpensive reagents, and reacts in the title reaction with acetonitrile, sodium chloride, and sodium methanesulfonate as the sole byproducts. Although this Communication focuses primarily on reactions with cyanide as nucleophile, preliminary experiments with other nucleophiles foreshadow the broad reaching synthetic utility of this approach.

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“…The reaction is hampered by isomerisation-in this case to give 65. The intramolecular cycloaddition (formally a Diels-Alder addition) of a diene tethered to a cyclobutadiene Fe-complex (66) gives tricyclic cyclobutene compound 67 (Scheme 22). A range of analogous reactions are also reported.…”

Section: Chromium Molybdenum and Tungstenmentioning

confidence: 99%

Chapter 3. Organometallic chemistry

Lloyd‐Jones¹

1999

Annu. Rep. Prog. Chem., Sect. B

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A selection of useful or unusual transition metal mediated reactions from the chemical literature of 1998 are reviewed below. Some reactions also involve transition metal catalysis in addition to the stoichiometric transition metal component. In all cases, the reactions are organised by the transition metal group of the stoichiometric component with further subdivisions by reaction class or intermediates. ApplicationsScandium, ytterbium and the lanthanides Stoichiometric applications of these metals are scarce. However, the dehydrogenative coupling of aromatic aldimines has been reported to occur on treatment with Yb metal and then an aromatic aldehyde as a hydrogen acceptor. Thus, for example, treatment of aldimine 1 with Yb and then 1-naphthaldehyde afforded dimine 2 in 81% yield (Scheme 1). Titanium, zirconium and hafniumOlefination. Olefinations involving dithioacetal desulfurisation by titanocene reagents has been reviewed.Metallocenes. Zirconacyclopentadiene intermediates, formed by reaction of zirconocene with acetylenes continue to be of interest. For example they may be crosscoupled with 3-iodopropenoates to afford cyclopentadienylacetate derivatives. Alternatively, the two C-Zr bonds can be selectively cleaved by halogenating agents such as NCS, NBS or I to afford 1,4-dihalogeno-1,3-dienes in good yield. Furthermore, reaction with 2-iodothiophene in the presence of CuCl and DMPU furnishes thienyl dienes. The intriguing cyclophane 4, in which each pyridine is anti (X-ray crystallography) was prepared by reaction of zirconocene with bisacetylene 3 (Scheme 2). The

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A Highly Chemo- and Regioselective N-Acylative Alkynylation of Quinolines with Alkynylsilanes Promoted by Triflate Ion

Abstract: Reactions of quinolines activated by phenyl chloroformate and silver triflate with 1-alkynylsilanes proceed smoothly at 83 °C to afford 1-alkynyl-1,2-dihydroquinolines in highly chemo- and regioselective manners.

Cited by 23 publications

References 12 publications

The organic chemistry of silver acetylides

The organic chemistry of silver acetylides

A Bifunctional Reagent Designed for the Mild, Nucleophilic Functionalization of Pyridines

Chapter 3. Organometallic chemistry

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