- Continuous flow magnesiation of functionalized heterocycles and acrylates with TMPMgCl·LiCl
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A flow procedure for the metalation of functionalized heterocycles (pyridines, pyrimidines, thiophenes, and thiazoles) and various acrylates using the strong, non-nucleophilic base TMPMgCl·LiCl is reported. The flow conditions allow the magnesiations to be performed under more convenient conditions than the comparable batch reactions, which often require cryogenic temperatures and long reaction times. Moreover, the flow reactions are directly scalable without further optimization. Metalation under flow conditions also allows magnesiations that did not produce the desired products under batch conditions, such as the magnesiation of sensitive acrylic derivatives. The magnesiated species are subsequently quenched with various electrophiles, thereby introducing a broad range of functionalities. Go with the flow: Flow conditions allow a practical metalation of functionalized heterocycles and various acrylates in the presence of the base TMPMgCl·LiCl (TMP=2,2,6,6-tetramethylpiperidyl). More convenient temperatures and very fast reaction times can usually be achieved by applying the flow conditions. Sensitive acrylic derivatives can be magnesiated under flow conditions. Furthermore, the flow reactions are readily scalable without further optimization.
- Petersen, Trine P.,Becker, Matthias R.,Knochel, Paul
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supporting information
p. 7933 - 7937
(2014/08/05)
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- Aminoguanidine hydrazone derivatives, process for producing the same and drugs thereof
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The present invention is to provide a compound of the formula: wherein the ring A is an optionally substituted 5- to 6-membered aromatic heterocyclic ring, the ring B an optionally substituted 5- to 6-membered aromatic homocyclic ring or an optionally sub
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Page column 105
(2010/11/29)
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- PROTONATION AND ELECTROPHILIC TRICHLOROMETHYLATION OF 2,5- AND 2,4-DICHLOROTHIOPHENES
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Trichloromethylation of 2,5-dichlorothiophene, 1, and 2,4-dichlorothiophene, 2, with CCl4 and AlCl3 has been studied.It could be shown that in the case of 1 the reaction was directed to position 3 with formation of 2,5-dichloro-3-(trichloromethyl)thiophene, 3, the process being complicated by the formation of the isomeric 3,5-dichloro-2-(trichloromethyl)thiophene, 4, and 4,5-dichloro-2-(trichloromethyl)thiophene, 5, as well as linked products, i.e. a mixture of bis(dichlorothienyl)dichloromethanes (6).Trichloromethylation of 3 smoothly leads to 4, along with a small amount of bis(3,5-dichloro-2-thienyl)dichloromethane.It has also been found that, as a result of protonation, under the effect of HCl and AlCl3, the 2,5-dichloro derivative 1 was converted into the 2,4-dichloro isomer 2, which, under the reaction conditions, exist in the form of ?-complex, i.e. the 2H-3,5-dichlorothiophenium ion, stable at room temperature.The mechanism of trichloromethylation of 1, including the ipso-attack by the CCl3+ cation and isomerization during protonation, is discussed.
- Belen'kii, Leonid I.,Gromova, Galina P.,Krayushkin, Mikhail M.
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p. 365 - 368
(2007/10/02)
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- New imidazole anti-fungal agents derived from benzothiophene. Part II
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1-thienyl)methyl>-1H-imidazoles 22, 1-thien-3-yl)(thienyl)methyl>-1H-imidazoles 25 and 1-thien-3-yl)methyl>-1H-imidazoles 28 have been synthesized and tested for anti-fungal activity.All compounds showed good activity against a broad spectrum of fungi (yeasts, dermatophytes).
- Moreno-Manas, Marcial,Cuberes, Ma. Rosa,Palacin, Celia,Raga, Manuel,Castello, Josep M.,Ortiz, Jose A.
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p. 477 - 482
(2007/10/02)
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