- Facile cuI-catalyzed arylation of azoles and amides using simple enaminones as efficient ligands
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(E)-3-(Dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one was found to be an excellent ligand for copper-catalyzed N-arylation of azoles and amides with aryl halides under mild conditions. The reaction took place at 82 C in MeCN with broad functional-group compatibility. A combination of the ligand and CuI proved to be an efficient catalytic system to promote the coupling reactions of aryl halides with azoles and amides.
- Cheng, Cungui,Sun, Gonglei,Wan, Jieping,Sun, Cuirong
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experimental part
p. 2663 - 2668
(2010/01/16)
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- N,N′-(Phenylmethylene)diacetamide analogues as economical and efficient ligands in copper-catalyzed arylation of aromatic nitrogen-containing heterocycles
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N,N′-(Phenylmethylene)diacetamide analogues which were simply prepared from the condensation reaction of an aldehyde with an amide or urea were found to be efficient ligands in copper-catalyzed coupling reaction of aryl halides with various azole nucleophiles. The newly developed ligand showed broad application scope in this conversion. Compounds including imidazoles, benzoimidazoles, pyrrole, indole, and benzotriazole were successfully arylated with diversified aromatic halides to give corresponding products in moderate to excellent yields. Georg Thieme Verlag Stuttgart.
- Wan, Jie-Ping,Chai, Yun-Feng,Wu, Jian-Mei,Pan, Yuan-Jiang
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experimental part
p. 3068 - 3072
(2009/06/28)
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- Selective N(1)-arylation of benzotriazole with activated aryl halides under conditions of phase transfer catalysis
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Arylation of 1H-1,2,3-benzotriazole with activated aryl halides in a medium of aromatic hydrocarbons under conditions of phase transfer catalysis with the use of inorganic bases and cetyltrimethylammonium bromide as a phase-transfer catalyst was studied.
- Beletskaya,Davydov,Gorovoi,Kardashov
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p. 1533 - 1536
(2007/10/03)
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- STUDIES ON FLUORINE CONTAINING HETEROCYCLIC COMPOUNDS: 4. REACTIONS OF 3-NITRO-4-CHLOROBENZOTRIFLUORIDE AND 3,5-DINITRO-4-CHLOROBENZOTRIFLUORIDE WITH FIVE MEMBERED HETEROCYCLES
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The reactions of 3-nitro-4-chlorobenzotrifluoride (1a) and 3,5-dinitro-4-chlorobenzotrifluoride (1b) with heterocycles (2-5) are described.Six S-linked and N-substituted heterocycles (6, 9-11, 13), such as 2-(2-nitro-4-trifluoromethylphenylthio)benzothiazole (9a), were prepared from the reactions of 1a with benzotriazole (2), 2-mercaptobenzothiazole (5a) and 2-mercaptobenzoxazole (5b) and from the reactions of 1b with 2, 1,2,4-triazole (3) and 5a in DMF respectively. 1a reacted with 2-mercaptothiazoline (4) to give the desired product 7 and bis(2-nitro-4-trifluoromethylphenyl) thioether (8). 3-(2-Benzoxazolyl)-2-benzoxazolinethione (15) was obtained from the reaction of 1b with 5b.The spectral data and elemental analyses were fully in accord with the proposed structures, and the possible mechanisms for these compounds and other by-products were discussed.
- Chen, Mei-Jin,Chi, Ching-Sung,Chen, Qing-Yun
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