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

dc.contributor.advisorHandy, Scott
dc.contributor.authorAlsubhi, Ameen
dc.contributor.committeememberKline, Paul
dc.contributor.committeememberBicker, Kevin
dc.contributor.departmentChemistryen_US
dc.date.accessioned2015-12-18T19:09:13Z
dc.date.available2015-12-18T19:09:13Z
dc.date.issued2015-08-10
dc.description.abstractConsidering 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.abstractInterestingly, 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.description.degreeM.S.
dc.identifier.urihttp://jewlscholar.mtsu.edu/handle/mtsu/4731
dc.publisherMiddle Tennessee State University
dc.subject4H-PYRAN DERIVATIVES
dc.subjectDEEP EUTECTIC SOLVENTS
dc.subjectMULTICOMPONENT COUPLING
dc.subject.umiChemistry
dc.subject.umiOrganic chemistry
dc.subject.umiPharmaceutical sciences
dc.thesis.degreegrantorMiddle Tennessee State University
dc.thesis.degreelevelMasters
dc.titleONE-POT MULTICOMPONENT COUPLING SYNTHESIS OF 2-AMINO-3-CYANO-4H-PYRAN DERIVATIVES USING DEEP EUTECTIC SOLVENTS (DES)
dc.typeThesis

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