A new series of pyridinyl-alkynes as antagonists of the metabotropic glutamate receptor 5 (mGluR5)

Bach, Peter; Nilsson, Karolina; Wållberg, Andreas; Bauer, Udo; Hammerland, Lance G.; Peterson, Alecia; Svensson, Tor; Österlund, Krister; Karis, David; Boije, Maria; Wensbo, David

doi:10.1016/j.bmcl.2006.06.079

Cited by 31 publications

(11 citation statements)

References 25 publications

(4 reference statements)

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“…For the preparation of 1,3‐diynyl propargyl aryl ethers 1 we chose the reaction of phenol with propargyl bromide in the presence of K 2 CO 3 in acetone at reflux for 24 h . After that, we installed the bromine in the alkyne using N ‐bromosuccinimide and silver nitrate .…”

Section: Resultsmentioning

confidence: 99%

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

2020

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The synthesis of selenophene‐fused chromene derivatives starting from 1,3‐diynyl propargyl aryl ethers is reported herein. The method is based on carbon‐carbon, carbon‐selenium, selenium‐carbon and carbon‐selenium bonds formation in a one‐pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1‐(butylselanyl)‐selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross‐coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n‐butyllithium.

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Section: Resultsmentioning

confidence: 99%

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

2020

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“…Treatment of the carboxylic acids 4b (R = OMe), 4c (R = Cl), and 4d (R = Me), with lithium aluminium hydride15 afforded the corresponding alcohols 5b , 5c and 5d in good yields. Subsequent oxidation of the alcohol using a stabilized form of 2‐iodoxybenzoic acid (sIBX), which is composed of o ‐iodoxybenzoic acid (49 %), benzoic acid (22 %) and isophthalic acid (29 %),16 gave the desired aldehydes17 6b , 6c and 6d in good overall yield.…”

Section: Resultsmentioning

confidence: 99%

Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydrobenzo[e]azulenes

et al. 2015

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“…Carbon–carbon triple bonds are important structural motifs in organic chemistry. They can be found in drug and drug candidate molecules, such as ethinylestradiol and mGluR5 receptor antagonists,1, 2 and enediyne antibiotics, such as Neocarzinostatin,3 and they provide ready access to numerous other functional groups via well‐precedented transformations. The synthetic accessibility of aryl alkynes was dramatically improved with the report of what has come to be known as the Sonogashira reaction in 1975 4.…”

Section: Introductionmentioning

confidence: 99%

Quantifying the anthropogenic fraction of fatty alcohols in a terrestrial environment

Mudge¹,

DeLeo

Dyer

2012

Enviro Toxic and Chemistry

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Fatty alcohols are naturally produced hydrocarbons present in all living organisms. They are also used in detergent and cosmetic formulations, may be sourced from either petroleum or biological materials, and are typically disposed of down the drain. This study was conducted on the Luray catchment, Virginia, USA, where sales data indicate that approximately 2 kg of fatty alcohols from detergent enter the wastewater every day. Reconstructing fatty alcohols in the influent on the basis of sales data indicated a mix of odd and even chain compounds, with C(12) being dominant. This profile was influenced strongly by liquid laundry detergents (69%). Sediment and soil samples from the catchment were analyzed by gas chromatography-mass spectrometry and by stable isotope ratio mass spectrometry to determine the δ(13)C and δ(2)H signatures. The long-chain components in agricultural soils and river sediments were distinguishable clearly from the algal fatty alcohols produced within the river system. The wastewater was a mixture of fecal and detergent sources of fatty alcohols in a ratio of 75:25%. The fatty alcohols in the effluent had different stable isotopic signatures and chain-length profiles from the influent, indicating that these compounds are not the same as those that entered the treatment plant. The total quantity of fatty alcohols leaving the treatment plant through the effluent pipe was low compared with the input. Analysis of the contributions based on the stable isotopes and profiles suggests that of the fatty alcohols present in the river system downstream of the treatment plant, 84% were derived from terrestrial plant production, 15% came from in situ algal synthesis, and 1% were derived from the effluent.

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A new series of pyridinyl-alkynes as antagonists of the metabotropic glutamate receptor 5 (mGluR5)

Cited by 31 publications

References 25 publications

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydrobenzo[e]azulenes

Quantifying the anthropogenic fraction of fatty alcohols in a terrestrial environment

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A new series of pyridinyl-alkynes as antagonists of the metabotropic glutamate receptor 5 (mGluR5)

Cited by 31 publications

References 25 publications

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

Iron‐Mediated Cyclization of 1,3‐Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene‐Fused Chromenes

Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydro­benzo[e]azulenes

Quantifying the anthropogenic fraction of fatty alcohols in a terrestrial environment

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Lewis Acid Catalyzed Cyclizations of Epoxidized Baylis–Hillman Products: A Straightforward Synthesis of Octahydrobenzo[e]azulenes