- Cobalt-catalyzed C-N bond-forming reaction between chloronitrobenzenes and secondary amines
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Cyclic secondary amines react with mono- or dichloronitrobenzene in the presence of a catalytic amount of cobalt(II) chloride. Phosphane ligands are beneficial for the reaction, although the bite-angle effect was not strong. The nitro-substituted tertiary amines formed are important as bioactive compounds and can also be intermediates for the synthesis of substituted anilines. This work represents the first cobalt-catalyzed approach to C-N bond-forming reactions involving aromatic chlorides and cyclic secondary amines. The reaction is ortho- and para-selective, with meta-substituted halides being unreactive in this procedure. The first cobalt-catalyzed C-N bond-forming reaction involving aromatic chlorides and cyclic secondary amines is described.The reaction is ortho- and para-selective; meta-substituted halides are unreactive. Copyright
- Toma, Gabriel,Yamaguchi, Ryohei
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experimental part
p. 6404 - 6408
(2011/02/22)
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- Reaction of Mono-, Di-, and Trichloronitrobenzenes with N-Methyl Substituted Cyclic Tertiary Amines under High Pressure
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The reactions of mono-, di-, and trichloronitrobenzenes with 1-methylpyrrolidine under high pressure gave products of demethylation and ring-opening through a quaternary pyrrolidinium chloride intermediate formed by the SNAr reaction.On the other hand, the reactions with 1-methylpiperidine and 4-methylmorpholine gave only demethylation products.The selectivities of the resctions of 1-methylpyrrolidine with these chloronitrobenzenes were found to be effected by the neighboring substituent to the pyrrolidinium group.
- Ibata, Toshikazu,Shang, Muhong,Demura, Tetsuo
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p. 2717 - 2726
(2007/10/03)
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- Aromatic Nucleophilic Substitution of Halobenzenes with Amines under High Pressure
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The nucleophilic substitution reactions of aromatic halides having electron-attracting groups on ortho or para position with various primary and secondary amines were accelerated by high pressure to give the corresponding N-substituted anilines in high yields.The bulkiness of amines affects its reactivity to lower the yields of the products.Although the secondary amines are usually less reactive than primary amines, cyclic secondary amines such as morpholine, piperidine, and pyrrolidine were found very reactive. 1,4-Diazabicyclooctane and quinuclidine gave N-quarternary ammonium halides in high yields in contrast to the low reactivity of acyclic tertiary amines.Dichloro- and trichloro-nitrobenzenes also react with diethylamine, pyrrolidine, and morpholine to give mono-, di-, and trisubstitution products depending upon the amount of amine and the position of nitro group in these chlorides.
- Ibata, Toshikazu,Isogami, Yasushi,Toyoda, Jiro
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- 9-(P-phenylazoanilino)-7-methyl-1H-imidazo[4,5-f]quinolines
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A series of 9-(substituted amino)imidazo[4,5-f]quinolines are effective anthelmintic agents; particularly in respect to the tapeworm Hymenolepis nana.
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