- A Novel One-Pot Synthesis of N,N-Dimethylaminopyridines by Diazotization of Aminopyridines in Dimethylformamide in the Presence of Trifluoromethanesulfonic Acid
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Abstract: Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid gives the corresponding pyridinyl trifluoromethanesulfonates instead of expected diazonium salts. Pyridinyl trifluoromethanesulfonates can be converted to N,N-dimethylaminopyridines on heating in dimethylformamide via replacement of the trifluoromethanesulfonyloxy group. The reaction is accelerated under microwave irradiation. A novel one-pot procedure has been proposed for the synthesis of 2- and 4-(dimethylamino)pyridines from commercially available aminopyridines. The procedure provides high yields of the target products, and it can be regarded as an alternative to the known methods of synthesis of N,N-dimethylpyridin-4-amine (DMAP) widely used as base catalyst in organic synthesis.
- Filimonov, V. D.,Krasnokutskaya, E. A.,Potapova, M. I.,Sanzhiev, A. N.
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p. 1023 - 1028
(2020/07/25)
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- Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides
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A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.
- Yang, Chu,Zhang, Feng,Deng, Guo-Jun,Gong, Hang
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p. 181 - 190
(2019/01/10)
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- Microwave irradiation-assisted amination of 2-chloropyridine derivatives with amide solvents
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A simple, quick, and high-yielding microwave-assisted synthesis of 2-(N,Ndimethyl) amine- and 2-aminopyridine derivatives is reported here for the first time in the reaction of 2-chloro substituted pyridines with amide solvents such as dimethylformamide or formamide, without transition-metal catalysts. Taylor & Francis Group, LLC.
- Samadi, Abdelouahid,Silva, Daniel,Chioua, Mourad,Carreiras, Maria Do Carmo,Marco-Contelles, Jose
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experimental part
p. 2859 - 2869
(2011/09/12)
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- A simple synthesis of aminopyridines: Use of amides as amine source
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A transition metal/microwave irradiation (or base) free synthesis of aminopyridines has been accomplished via C-N bond forming reaction between chloropyridine and a variety of simple amides under refuxing conditions.
- Kodimuthali, Arumugam,Mungara, Anitha,Prasunamba, Padala Lakshmi,Pal, Manojit
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experimental part
p. 1439 - 1445
(2010/11/04)
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- Microwave-induced by-products in the synthesis of 2-(4-methyl-2-phenylpiperazinyl)pyridine-3-carbonitrile
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The Letter describes the investigation of an industrial reaction of N-methylphenylpiperazine and chloronicotinonitrile, under microwave heating. Besides the formation of the expected 2-(4-methyl-2-phenylpiperazinyl)pyridine-3-carbonitrile (4), extension o
- Lamazzi, Christelle,Dreau, Armelle,Bufferne, Christel,Flouzat, Christine,Carlier, Patrick,ter Halle, Rob,Besson, Thierry
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scheme or table
p. 4502 - 4505
(2009/11/30)
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