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ONE-POT MULTICOMPONENT COUPLING SYNTHESIS OF 2-AMINO-3-CYANO-4H-PYRAN DERIVATIVES USING DEEP EUTECTIC SOLVENTS (DES)

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dc.contributor.advisor Handy, Scott
dc.contributor.author Alsubhi, Ameen
dc.date.accessioned 2015-12-18T19:09:13Z
dc.date.available 2015-12-18T19:09:13Z
dc.date.issued 2015-08-10
dc.identifier.uri http://jewlscholar.mtsu.edu/handle/mtsu/4731
dc.description.abstract Considering the importance of 2-Amino-3-cyano-4H-pyran derivatives and the need for the development of new environmental friendly synthetic methodologies, the combination of Multicomponent Coupling reactions (MCR) and Deep Eutectic solvents (DES) was the goal of our study in order to make the reaction more environmentally, as well as economically, viable. Moreover, a simple work up procedure was developed via recrystallization from ethanol or ethanol-water to avoid the use of expensive silica gel chromatography and exclude the massive use of organic chromatography eluents. Finally, this work avoids the use of toxic and expensive catalyst or solvents.
dc.description.abstract Interestingly, increasing the reaction scale from 1 mmol to 3 mmol improved the reaction isolated yield. A variety of substituted aromatic as well as heteroaromatic aldehydes were explored using the larger 3 mmol scale. Generally, electron withdrawing groups (EWG) on the aldehyde produced lower yields comparing with the electron donating groups (EDG). Lastly, an evaluation of the sequence addition off the reaction components was performed. The study shows that by mixing benzaldehyde, malononitrile, and adding dimedone after five minutes, in accordance with the Mantelingu procedure, the yield increases dramatically and the side reactions are limited.
dc.publisher Middle Tennessee State University
dc.subject 4H-PYRAN DERIVATIVES
dc.subject DEEP EUTECTIC SOLVENTS
dc.subject MULTICOMPONENT COUPLING
dc.title ONE-POT MULTICOMPONENT COUPLING SYNTHESIS OF 2-AMINO-3-CYANO-4H-PYRAN DERIVATIVES USING DEEP EUTECTIC SOLVENTS (DES)
dc.type Thesis
dc.contributor.committeemember Kline, Paul
dc.contributor.committeemember Bicker, Kevin
dc.thesis.degreelevel Masters
dc.thesis.degreegrantor Middle Tennessee State University
dc.subject.umi Chemistry
dc.subject.umi Organic chemistry
dc.subject.umi Pharmaceutical sciences
dc.description.degree M.S.
dc.contributor.department Chemistry en_US


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