Efficient Synthesis of 5H-Cyclopenta[c]quinoline Derivatives via Palladium-Catalyzed Domino Reactions of o-Alkynylhalobenzene with Amine

Abstract

A novel and efficient route for the synthesis of 5H-cyclopenta[c]quinoline derivatives via a palladium-catalyzed domino reaction of o-alkynylhalobenzene with amine is described. The starting materials are easily available, and the reaction proceeds smoothly with high efficiency, which shows broad scope with good functional group tolerance.

Green synthesis of polysubstituted quinoline and benzoquinoline derivatives in ionic liquid via a three-component reaction

“…Different imidazolium ionic liquids were also tested, and [BMIm]Br appeared to be the best solvent for this transformation (entry 3 vs. 5-9). Acidic ionic liquids, such as [BMIm][HSO 4 ], or acidic catalysts, for example, TsOH and AgOTf, were used to further improve the yields of the product 4a, to our disappointed, the results are not good (Table 1, entries [10][11][12].…”

“…The United States government-sponsored clinical trials for antimalarial drug development showed unequivocally that chloroquine has a significant therapeutic value as an antimalarial drug. Accordingly, novel strategies for the synthesis of quinolines continued to receive considerable attention in the field of organic synthetics chemistry [8][9][10][11][12][13].…”

Generation of Indene Derivatives by Tandem Reactions

“…19 When the reaction was performed in the presence of palladium(II) acetate (5 mol%), tricyclohexylphosphine (10 mol%), and potassium tert-butoxide in refluxing 1,4-dioxane, the indene-containing polycycle 38 was obtained in 85% yield. Mechanistic studies showed that this novel pathway involves a double carbopalladation.…”

Cascade Palladium‐ and Copper‐Catalysed Aromatic Heterocycle Synthesis: The Emergence of General Precursors

“…After two hours the required N-nucleophile was added along with additional base, resulting in the desired aryl amination followed by ring closure. [20] Scheme 7. Access to further heterocyclic derivatives such as 7-azaindoles and thienopyrroles can also be accomplished by use of the corresponding ortho-alkynylhalopyridine or orthoalkynylhalothiophene substrates, respectively.…”