Mercury in organic chemistry. 26. Synthesis of heterocycles via intramolecular solvomercuration of aryl acetylenes

Larock, Richard C.; Harrison, L. W.

doi:10.1021/ja00327a026

Cited by 146 publications

(101 citation statements)

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“…Silica gel column chromatography was performed using Merck silica gel 60 ASTM (70-230 mesh). 2-Iodothioanisole (5a) [12] and 3-iodothioanisole (5b) [13] were synthesized in 91% and 76% yields, respectively, starting from 2-(methylthio)aniline and 3-(methylthio)aniline using the procedure of Ullmann [14]. All other reagents, purchased from the Aldrich Chemical Company (Milwaukee, WI), were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of new 1‐(2‐, 3‐, or 4‐methanesulfonylphenyl)‐2‐[5‐(N‐hydroxypyridin‐2(1H)‐one)]acetylene regioisomers: A search for novel cyclooxygenase and lipoxygenase inhibitors

Chowdhury

Chen

Abdellatif

et al. 2009

Journal of Heterocyclic Chem

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A group of acetylene regioisomers were designed such that a cyclooxygenase-2 (COX-2) SO 2 Me pharmacophore was located at the ortho-, meta-, or para-position of the acetylene C-1 phenyl ring, and an iron-chelating 5-lipoxygenase (5-LOX) N-hydroxypyridin-2(1H)-one moiety was attached via its C-5 position to the C-2 position on an acetylene template (scaffold). These target linear acetylene regioisomers were synthesized via a palladium-catalyzed Sonogashira cross-coupling reaction. Structure-activity data acquired using in vitro cell-based inhibition assays indicated that this novel class of 1-(2-, 3-, or 4-methanesulfonylphenyl)-2-[5-(N-hydroxypyridin-2(1H)-one)]acetylene regioisomers did not inhibit the COX-2 or (5-LOX) enzymes, and that they are devoid of in vivo anti-inflammatory activities.

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Section: Methodsmentioning

confidence: 99%

Synthesis of new 1‐(2‐, 3‐, or 4‐methanesulfonylphenyl)‐2‐[5‐(N‐hydroxypyridin‐2(1H)‐one)]acetylene regioisomers: A search for novel cyclooxygenase and lipoxygenase inhibitors

Chowdhury

Chen

Abdellatif

et al. 2009

Journal of Heterocyclic Chem

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“…Starting Materials: Propargylic alcohols 1a, [27] 1b, [28] 1c, [29] 1d, [27] 1f, [30] 1g, [31] 1k, [32] 1l, 1m, 1n, 1o, [33] 1p, 1q, 1r, 1s, [34] 1t, 1u, [35] 1v, [36] and 1w [37] were synthesized through the reaction of the corresponding lithium acetylides and aldehydes. Propargylic alcohols 1e, 1h, and 6a were commercially available.…”

Section: Experimental Section General Methodsmentioning

confidence: 99%

Cationic Rhodium(I)/Bisphosphane Complex‐Catalyzed Isomerization of Secondary Propargylic Alcohols to α,β‐Enones

Tanaka¹,

Shoji²,

Hirano³

2007

Eur J Org Chem

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We have determined that hydrogenated cationic Rh(I)/ bisphosphane complexes are highly active catalysts for the isomerization of secondary propargylic alcohols to α,β-enones. A kinetic resolution of secondary propargylic alcohols proceeded with moderate selectivity with [Rh((R)-BINA-P)]OTf as a catalyst. Mechanistic studies revealed that the isomerization proceeds through intramolecular 1,3-and 1,2-hydrogen migration pathways. The isomerization of propargylic diol derivatives was also investigated, which revealed

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“…[62] Hg remains attached to the heterocycle, thus the process is non-catalytic and the corresponding benzofurane is obtained only after NaBH 4 reduction (Scheme 26, condition A).…”

Section: Cycloalkoxylation Of Alkynylphenolsmentioning

confidence: 99%

Similarities and Differences between the “Relativistic” Triad Gold, Platinum, and Mercury in Catalysis

2011

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Relativistic effects in the valence shell of the elements reach a maximum in the triad Pt-Au-Hg and determine their catalytic activity in organic reactions. In this Review we examine the catalytic activity of Pt, Au, and Hg compounds for some representative reactions, and discuss the respective benefits and disadvantages along with other relevant properties, such as toxicity, price, and availability. For the reactions considered, gold catalysts are generally more active than mercury or platinum catalysts.

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Mercury in organic chemistry. 26. Synthesis of heterocycles via intramolecular solvomercuration of aryl acetylenes

Cited by 146 publications

References 0 publications

Synthesis of new 1‐(2‐, 3‐, or 4‐methanesulfonylphenyl)‐2‐[5‐(N‐hydroxypyridin‐2(1H)‐one)]acetylene regioisomers: A search for novel cyclooxygenase and lipoxygenase inhibitors

Synthesis of new 1‐(2‐, 3‐, or 4‐methanesulfonylphenyl)‐2‐[5‐(N‐hydroxypyridin‐2(1H)‐one)]acetylene regioisomers: A search for novel cyclooxygenase and lipoxygenase inhibitors

Cationic Rhodium(I)/Bisphosphane Complex‐Catalyzed Isomerization of Secondary Propargylic Alcohols to α,β‐Enones

Similarities and Differences between the “Relativistic” Triad Gold, Platinum, and Mercury in Catalysis

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