CHICHIBABIN REACTION PDF

We'd like to understand how you use our websites in order to improve them. Register your interest. Among the dimethylaminopyridines, the 3- and 4-isomers are more active in the Chichibabin reaction, while 2-dimethylaminopyridine is converted with great difficulty under the action of sodium amide into 2,6-diaminopyridine with the initial replacement of the dimethylamine residue by an amino group. Azaindoles and azaindolines do not take part in the animation reaction.

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The Chichibabin reaction, an amination first discovered in [1], can install a primary amino group —NH 2 at the C2 position of pyridine derivatives using, e. However, the reaction usually needs harsh reaction conditions.

In addition, only a few successful examples of the reaction using primary alkyl amines have been reported. This is probably due to the inaccessibility of the corresponding alkyl metal amides. Shunsuke Chiba, Nanyang Technological University, Singapore, and colleagues have developed a concise protocol for the Chichibabin amination that allows efficient access to a range of 2-aminopyridines and their derivatives under mild reaction conditions. The reaction introduces the desired primary alkyl amines at the C2 position in good to excellent yields.

The method can be scaled up to a mmol-scale. It can also be extended to a double amination of 2,2'-bipyridines for the construction of a series of 6,6'-bis alkylamino -2,2'-bipyridines example pictured. Please note that to comment on an article you must be registered and logged in.

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The Chichibabin reaction in the Aminopyridine, azaindole, and azaindoline series

The Chichibabin reaction, an amination first discovered in [1], can install a primary amino group —NH 2 at the C2 position of pyridine derivatives using, e. However, the reaction usually needs harsh reaction conditions. In addition, only a few successful examples of the reaction using primary alkyl amines have been reported. This is probably due to the inaccessibility of the corresponding alkyl metal amides. Shunsuke Chiba, Nanyang Technological University, Singapore, and colleagues have developed a concise protocol for the Chichibabin amination that allows efficient access to a range of 2-aminopyridines and their derivatives under mild reaction conditions.

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It was reported by Aleksei Chichibabin in The direct amination of pyridine with sodium amide takes place in liquid ammonia. Ciganek describes an example of an intramolecular Chichibabin reaction in which a nitrile group on a fused ring is the source of nitrogen in amination. The hydride ion abstracts a hydrogen from the positively charged nitrogen, forming hydrogen gas.

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