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Dr. Daryoush Tahmassebi
Department of Chemistry
Indiana University – Purdue University Fort Wayne
N-arlquinolines derivatives are an important class of heterocyclic compounds having important pharmaceutical and biological activities. These compounds are used as antiplasmodial, intrinsic, cytotoxic, functional, antibacterial, antiproliferative, antimalarial, and even anti-cancer. The current methods of synthesis for these compounds such as; Skraup, Doebner-Von Miller, Conrad Limbach, Combes and Pfitzinger are unappealing to many. These methods are either costly, dangerous, time consuming or inefficient.
In this presentation we report 1,4-Diazabicyclo[2.2.2]octane known as DABCO as an efficient catalyst for one-pot multicomponent synthesis of 2-Amino-7-7-dimethyl-5-oxo-1,-diphenyl- 1,4,5,6,7,8-hexahydroquinoline-3-carbonitriles from aromatic aldehydes, malononitrile, and 3- aryl-5,5-dimethyl-cyclohex-2-en-1-ones in DMF at room temperature. This procedure is an efficient and environmentally friendly approach for preparing N-arlquinonlines derivatives that offers many other advantages over previous methods such as: short reaction time, high yielding products, low cost, a high level of ease, and straight forward work-up.
Different aromatic aldehydes have been used to show the general catalytic application of DABCO for this reaction. All products were completely characterized via spectroscopy methods, such as IR and NMR as well as melting points. Different features of this reaction will be presented at the symposium.
Chemistry | Physical Sciences and Mathematics
Gerardot, Shori, "One-Pot Three Component Synthesis of N-Arulquinolines" (2014). 2014 IPFW Student Research and Creative Endeavor Symposium. 50.