AI Article Synopsis
- A new method was developed to efficiently create 1,2-dihydroquinolines by reacting an aniline with two ketones, using magnesium bromide as a catalyst in a solvent-free environment.
- The reaction showed a preference for producing mainly one specific product, even when using different types of anilines and nonsymmetrical ketones.
- The research included an exploration of the reaction mechanism, suggesting that an imine forms first from the aniline and one ketone before the final ring structure is created.
Article Abstract
A highly efficient and regioselective synthesis of 1,2-dihydroquinolines via a multicomponent reaction between an aniline and two ketones is described. This reaction was catalyzed by magnesium bromide and carried out under solvent-free conditions. When the reaction was performed by using 3-substituted anilines and nonsymmetrically substituted ketones, principally a single product was found among the four expected regioisomers. A variety of anilines and ketones, including cyclic ketones, were evaluated providing a series of 1,2-dihydroquinolines with diverse substitution patterns. A study of the mechanism is discussed. There is evidence of the in situ formation of the imine as a result of the reaction between the aniline and one of the ketones, before annulation to the heterocyclic ring.
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| http://dx.doi.org/10.1021/jo400973g | DOI Listing |
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