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Chemoselective Divergent Transformations of N-(Propargyl)indole-2-carbonitriles with Nitrogen Nucleophiles: Alkyne Hydroamination or Domino Cyclizationsстатья
Статья опубликована в высокорейтинговом журнале
Статья опубликована в журнале из списка Web of Science и/или Scopus- Авторы: Zalte R.R., Festa A.A., Raspertov P.V., Storozhenko O.A., Golantsov N.E., Rybakov V.B., Varlamov A.V., Voskressensky L.G.
- Журнал: Journal of Organic Chemistry
- Том: 87
- Номер: 21
- Год издания: 2022
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 13663
- Последняя страница: 13671
- DOI: 10.1021/acs.joc.2c01327
- Аннотация: Interactions of N-(propargyl)indole-2-carbonitriles with nitrogen nucleophiles were studied. It was found that lithium hexamethyldisilazane (LiHMDS)-promoted reactions give mixtures of two product types, originating from an initial attack onto carbon-carbon or carbon-nitrogen triple bonds. Performing the reaction at reduced temperature and in the presence of catalytic amounts of LiHMDS delivered alkyne hydroamination products exclusively. On the contrary, the one-pot reaction of N-(propargyl)indole-2-carbonitriles with methanol and LiHMDS on heating, followed by the addition of a nitrogen nucleophile, allowed a selective domino cyclization sequence toward 1-aminopyrazino[1,2-a]indoles. Anilines and nitrogen heterocycles could be employed as N-nucleophiles to obtain products of both types. Moreover, an alternative one-pot route toward a third product type has been developed. When N-(propargyl)indole-2-carbonitrile was first combined with aniline and LiHMDS at reduced temperature, further heating of the in situ generated hydroamination product led to the intramolecular cyclization into 1-imino-2-phenylpyrazino[1,2-a]indoles. Thus, chemodivergent transformations of the same starting material into three compound classes were investigated. The possible reaction routes were studied, and N-(allenyl)indole-2-carbonitrile was identified as the key intermediate. Acyclic and cyclic products exhibit fluorescence emission in the blue to green range. © 2022 American Chemical Society. All rights reserved.
- Добавил в систему: Малошицкая Ольга Александровна