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1,4-Diazabicyclo[2.2.2]octanium Diacetate under Grinding: Efficient and Eco-Friendly Process for the Synthesis of Symmetric, Unsymmetric and New Bis di(indolyl)indolin-2-one

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Background: A facile, effective, new and green methodology has been developed for the synthesis of 3,3-di(indolyl)indolin-2-one through electrophilic condensation reaction of indole derivatives with various isatins in the presence of 1,4-diazabicyclo[2.2.2]octanium diacetate as an efficient homogeneous media under grinding. This work consistently has advantages as excellent yields, short reaction time, mild condition and simple work-up procedures. The catalyst could be easily recovered and reused for six cycles with almost consistent activity. All of the synthesized compounds were characterized by their physical constant, comparison with authentic samples, IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.

Methods: A mixture of isatin derivatives (1 mmol) or synthesized bis isatin (0.5 mmol), indole derivatives (2 mmol) and [DABCO] dihydroacetate (0.5 mmol) were added to a mortar and the mixture was pulverized with a pestle for the required reaction time. After completion of the reaction, as indicated by TLC, the reaction mixture was dissolved in 20mL of H2O. The product was separated by filtration and recrystallized from EtOH and dried to afford powdery compounds 3a-n. The filtrate was concentrated under reduced pressure and washed with diethyl ether. Then, it was dried in a vacuum evaporator to recover the ionic liquid for subsequent use.

Results: In continuation of our ongoing studies to synthesize heterocyclic and pharmaceutical compounds under mild and practical protocols, herein we wish to report our experimental results on the synthesis of 3,3-di(indolyl)indolin-2-one using various isatins and indoles in the presence of novel ionic liquid ([DABCO]diactate). After the reaction, the used ionic liquid was separated and recycled to use for the next reaction run. Our experiments also indicated that after five runs, the catalytic activities of the reagents were almost the same as those of fresh catalysts.

Conclusion: In conclusion, we have investigated DABCO-diacetate as a mild and efficient catalyst for the synthesis of oxindoles. This method should be useful from the industrial point of view because it is high yielding and time saving under solvent free condition. DABCO-diacetate is inexpensive, nontoxic, easy to handle, and can act as a green medium. Simple work-up procedure, short reaction times, high yields of product with better purity, and green aspect due to the recyclability of media are major advantages of this protocol.
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Keywords: 1; 3; 3-di(indolyl)indolin-2-one; 4-diazabicyclo [2.2.2] octanium diacetate; DABCO; Solvent free; isatin; symmetric

Document Type: Research Article

Publication date: August 1, 2017

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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