117569-57-0Relevant articles and documents
Utilizing a copper-free Sonogashira reaction in the synthesis of the leukotriene a4 hydrolase modulator batatasin IV
Petruncio, Greg,Girgis, Michael,Moummi, Sanae,Jayatilake, Meth,Lee, Kyung Hyeon,Paige, Mikell
, (2020)
Batatasin IV is a dihydrostilbenoid isolated from Chinese yams which was shown to have inhibitory activities against plant growth. Later studies showed that this compound may exhibit anti-inflammatory properties by inhibiting the epoxide hydrolase activity of the leukotriene A4 hydrolase enzyme. To access the dihydrostilbenoid skeleton, a copper-free SPhos-mediated Sonogashira reaction was conceived and the substrate scope was explored. Our results indicate that the reaction can tolerate the presence of free alcohols, aldehydes, nitro groups, and anilinyl groups. However, a substituent with an acidic phenol or carboxylic acid group gave significantly lower yields. Next, a total synthesis of batatasin IV was accomplished in 16% overall yield incorporating the reported copper-free Sonogashira reaction. Finally, we show that batatasin IV inhibits the hydrolysis of alanine p-nitroanilide by leukotriene A4 hydrolase with an IC50 of 91.4 μM.
Hydrazinoaminocarbene-palladium complexes as easily accessible and convenient catalysts for copper-free Sonogashira reactions
Savicheva, Elizaveta A.,Kurandina, Daria V.,Nikiforov, Vladimir A.,Boyarskiy, Vadim P.
, p. 2101 - 2103 (2014)
Two easily accessible hydrazinoaminocarbene complexes of Pd(II) are shown to be efficient catalysts for copper-free Sonogashira cross-couplings of a variety of aryl iodides with aryl- and alkylalkynes under mild conditions, in ethanol as the solvent and u
Acceleration of photoinduced charge separation in porphyrin-C60 dyad with an acetylene spacer
Yamada, Koji,Imahori, Hiroshi,Nishimura, Yoshinobu,Yamazaki, Iwao,Sakata, Yoshiteru
, p. 895 - 896 (1999)
A porphyrin-C60 dyad with an acetylene spacer has been synthesized for the first time. The rate constant for charge separation in the dyad is larger by a factor of about three compared with a porphyrin-C60 dyad with an amide spacer,
Polyethylenes bearing a terminal porphyrin group
Unterlass, Miriam M.,Espinosa, Edgar,Boisson, Fernande,D'Agosto, Franck,Boisson, Christophe,Ariga, Katsuhiko,Khalakhan, Ivan,Charvet, Richard,Hill, Jonathan P.
, p. 7057 - 7059 (2011)
An α-[Cu(ii)-porphyrin]-polyethylene was synthesized for the first time using copper catalyzed 1,3-dipolar azide-alkyne Huisgen cycloaddition yielding highly colored moiety-substituted polyethylene.
Synthesis and Simple Immobilization of Palladium(II) Acyclic Diaminocarbene Complexes on Polystyrene Support as Efficient Catalysts for Sonogashira and Suzuki-Miyaura Cross-Coupling
Mikhaylov, Vladimir N.,Sorokoumov, Viktor N.,Korvinson, Kirill A.,Novikov, Alexander S.,Balova, Irina A.
, p. 1684 - 1697 (2016/07/06)
Immobilization of palladium(II) acyclic diaminocarbene (Pd(II)-ADC) complexes on a resin support surface has been easily performed by metal-mediated addition of amino groups of benzhydrylamine-polystyrene to the coordinated isocyanide ligand of cis-PdCl2(CNR)2 (R = t-Bu, Cy). The investigation of the benzhydrylamine reaction with palladium-coordinated isocyanides in solution has revealed that, depending on the reaction conditions, two carbene-type complexes can be obtained as a result of the addition to the CN triple bond, as well as a third complex which is formed via substitution of the isocyanide ligand by benzhydrylamine. Nucleophilic addition of an amino group to the isocyanide ligand has led to a cis-acyclic diaminocarbene complex or a cationic diaminocarbene complex with trans configuration and an intramolecular hydrogen-bonded chloride anion (the nature of this noncovalent interaction was analyzed by DFT calculations, including AIM analysis). The unsupported and resin-supported palladium catalysts have demonstrated high catalytic activity in both Sonogashira and Suzuki-Miyaura cross-coupling. The supported catalyst can be recovered and repeatedly reused without a significant loss in efficiency. The degree of the palladium binding with polystyrene, the oxidation state, and the palladium leaching level were investigated by XPS and XRF analyses.
Palladium-Catalyzed Nitration of Meyer-Schuster Intermediates with tBuONO as Nitrogen Source at Ambient Temperature
Lin, Yuanguang,Kong, Weiguang,Song, Qiuling
supporting information, p. 3702 - 3705 (2016/08/16)
A novel domino palladium-catalyzed nitration of Meyer-Schuster intermediates which were generated in situ from propargylic alcohols was developed, by the use of t-BuONO, leading to α-nitro enones in good to excellent yields at room temperature with a broa
SUBSTITUTED 1-AMINOPHTHALAZINE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC APPLICATION THEREOF
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Page/Page column 54, (2009/05/28)
The invention concerns 1-amino-phthalazine derivatives of general formula (I): Wherein A, B, L, R, R1, R2, R3, R4, R5 and R7 are as defined herein. The invention also concerns the preparation of said compounds and their therapeutic use.
Cross-coupling of aryl iodides with paramagnetic terminal acetylenes derived from 4,4,5,5-tetramethyl-2-imidazoline-2-oxyl 3-oxide
Klyatskaya, S. V.,Tretyakov, E. V.,Vasilevsky, S. F.
, p. 128 - 134 (2007/10/03)
2-(Arylylethynylphenyl)-4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxides 12 and 13 were synthesized by cross-coupling of aryl iodides with 1-alkynes containing the 4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxide fragment. A procedure was developed for the preparation of 3-and 4-ethynyibenzaldehydes with the use of 2-methylbut-3-yn-2-ol.
Process for the preparation of ethynylbenzaldehydes
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, (2008/06/13)
A multi-step process for the preparation of ethynylbenzaldehydes from bromo- or iodobenzaldehydes is disclosed. The arylhalogen is replaced with a protected ethynyl compound which is subsequently cleaved by base to form the arylacetylene. The aldehydic functionality is preserved by formation of a corresponding Schiff's base or acetal, and its subsequent regeneration by treatment with aqueous acid.
