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Articles 1 - 13 of 13

Full-Text Articles in Organic Chemistry

Computational Study Of Lawesson’S Reagent Mediated Fluorenone Dimerization Forming 9,9’-Bifluorenylidene, Andrew Jourdan Eckelmann May 2018

Computational Study Of Lawesson’S Reagent Mediated Fluorenone Dimerization Forming 9,9’-Bifluorenylidene, Andrew Jourdan Eckelmann

MSU Graduate Theses

The ambition of this work is to start a path to the a priori rational design of high yield production for electron acceptors with finely tuned band gaps, from the comfort of an armchair. To this end, organic photovoltaics offer a cheap and sustainable means of manufacture using readily available materials and avoids the toxicity of some of the heavy metals used in first and second-generation solar cells such as cadmium. The microwave assisted Lawesson’s reagent mediated one-pot one-step solventless synthesis takes less than 3 minutes and results in an 84% yield of 9,9’-bifluorenylidene from two equivalents ...


Formation Of Highly Functionalized Indole Through Carbon-Carbon Bond Cleavage, Ryan A. S. Pike Nov 2017

Formation Of Highly Functionalized Indole Through Carbon-Carbon Bond Cleavage, Ryan A. S. Pike

Chemistry ETDs

Indoles are one of the most abundant heterocycles found in nature and have a wide range of functions. There are a wide variety of indole synthesis methods known both in synthetic chemistry and through biosynthesis. Many of the known indole synthesis routes use a benzene derivative or cyclized ring structure derivative as a starting material. Here, we describe a novel synthetic method utilizing 1, 3-diketones and fumaronitrile with a catalytic amount of base to form a highly functionalized indole as our product. We have isolated and characterized 12 functionalized indoles.


Synthesis, Characterization And Evaluation Of Lectin-Binding Properties Of 1,2-Cis-Glycosides, Bo Meng Aug 2015

Synthesis, Characterization And Evaluation Of Lectin-Binding Properties Of 1,2-Cis-Glycosides, Bo Meng

Doctoral Dissertations

This dissertation presents a state-of-the-art research of 1,2-cis-glycosides, including synthetic methodology development, combinatorial total synthesis of galactoside ligands, construction of glycomicroarray surfaces, and quantitative evaluation of carbohydrate–lectin binding properties.

In Chapter 1, as a general introduction, various strategies that have been developed for the stereoselective construction of 1,2-cis-O-glycosidic bond are reviewed. 1,2-cis-O-Glycoside structural units are ubiquitous in nature, and they are extensively involved in numerous biological activities. The systematic identification and evaluation of the roles of carbohydrates usually relies on practical synthetic approaches to afford pure carbohydrates in ...


Strategies For Photochemical And Thermal Modification Of Materials, Sara Ghiassian Jul 2015

Strategies For Photochemical And Thermal Modification Of Materials, Sara Ghiassian

Electronic Thesis and Dissertation Repository

The modification of materials/surfaces is central to numerous applications ranging from opto-electronic devices to biomedical implants and drug delivery. Thus, there exists a high motivation for improving the methodologies which can be employed in order to modify surfaces in a selective and efficient fashion. One of the major goals of surface engineering is to control the chemical composition at the material interface. The fine control of the surface properties is a field of intense research as the performance of functional materials is strongly related to the processes and interactions that are occurring at the materials’ interface.

In general, the ...


New Methods For Synthesis Of Organic Peroxides And Application Of Peroxide Electrophiles To Synthesis Of Functionalized Ethers, Shiva Kumar Kyasa Apr 2015

New Methods For Synthesis Of Organic Peroxides And Application Of Peroxide Electrophiles To Synthesis Of Functionalized Ethers, Shiva Kumar Kyasa

Student Research Projects, Dissertations, and Theses - Chemistry Department

New Method for Synthesis of Alkyl Hydroperoxides: There are a number of methods reported for synthesis of alkyl hydroperoxides, but most of them suffer either from poor yields or the formation of unwanted side products. I will be discussing new methodology for efficient synthesis of pure samples of 1° and 2° alkyl hydroperoxides via alkylation of readily available cyclododecanone 1,1-dihydroperoxide followed by hydrolysis of the resulting bis peroxyacetals.

Peroxide Electrophiles for Synthesis of Functionalized Ethers: Peroxides are underexplored functional groups as precursors for C-O bond formation and ether synthesis. The reactivity of dialkyl peroxides towards organometallics such as alkyl ...


Diels-Alder Synthesis Of Novel Heterocyclic Compounds, Including Inverse-Electron-Demand And Microwave Promotion, Kristen Richey Apr 2015

Diels-Alder Synthesis Of Novel Heterocyclic Compounds, Including Inverse-Electron-Demand And Microwave Promotion, Kristen Richey

Honors Program Projects

One of the main subjects of this research is to compare “inverse-electron-demand” Diels-Alder (IED-DA) reactions with the classical, or “normal-electron-demand” (NED), DA reactions in an attempt to further define the line between the two. The other main focus is to compare methods using conventional heat with using microwave promotion. In both cases, the goal was to produce novel heterocyclic compounds.


Inhibition Of The Thioesterase Activity Of Human Fatty Acid Synthase By 1,4- And 9,10-Diones, Herman H. Odens Sep 2014

Inhibition Of The Thioesterase Activity Of Human Fatty Acid Synthase By 1,4- And 9,10-Diones, Herman H. Odens

Faculty Works

Fatty acid synthase (FASN) is the enzyme that synthesizes fatty acids de novo in human cells. Although FASN is generally expressed at low levels in most normal tissues, its expression is highly upregulated in many cancers. Consistent with this notion, inhibition of FASN activity has demonstrated potential to halt proliferation and induce cell death in vitro and to block tumor growth in vivo. Consequently, FASN is widely recognized as a valuable therapeutic target. In this report, we describe a variety of 1,4-quinones and 9,10- anthraquinones, including several natural compounds and some newly synthesized compounds, that potently inhibit the ...


Studies On The Synthesis Of Orthogonally Protected Azalanthionines, And Of Routes Towards B-Methyl Azalanthionines, By Ring-Opening Of N-Activated Aziridine-2-Crboxylates, Keith O'Brien, Keith Ó Proinsias, Fintan Kelleher Jun 2014

Studies On The Synthesis Of Orthogonally Protected Azalanthionines, And Of Routes Towards B-Methyl Azalanthionines, By Ring-Opening Of N-Activated Aziridine-2-Crboxylates, Keith O'Brien, Keith Ó Proinsias, Fintan Kelleher

Articles

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para-methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding b-methyl azalanthionines have, so far, been unsuccessful.


Synthesis Of Orthogonally Protected 1,2-Diaminopropanoic Acids By Ring-Opening Of 3-Unsubstituted N-Activated Aziridine 2-Carboxylates With Para-Methoxybenzylamine: A Study Of The Regioselectivity Of The Reaction, Fintan Kelleher, Keith O'Brien Oct 2013

Synthesis Of Orthogonally Protected 1,2-Diaminopropanoic Acids By Ring-Opening Of 3-Unsubstituted N-Activated Aziridine 2-Carboxylates With Para-Methoxybenzylamine: A Study Of The Regioselectivity Of The Reaction, Fintan Kelleher, Keith O'Brien

Articles

Orthogonally protected 1,2-diaminopropanoic acids (DAPs) have been synthesised in good yields by the ring-opening of 3-unsubstituted N-activated aziridine 2-carboxylates with para-methoxybenzylamine. The choice of both the N-activating group and ester alkyl group had a significant influence on the ratio of attack at the a or b positions of the aziridine. However, the regiochemical outcome is not predictable.


1,2,4-Triazine-Accelerated Azide-Alkyne Cycloaddition And Synthesis Of Metalloenzyme Inhibitors, Belinda Shea Lady May 2013

1,2,4-Triazine-Accelerated Azide-Alkyne Cycloaddition And Synthesis Of Metalloenzyme Inhibitors, Belinda Shea Lady

Doctoral Dissertations

The work of this dissertation describes the design and synthesis of 1,2,4-triazine ligands and other N-containing heterocycles and their use in the copper-catalyzed azide-alkyne cycloaddition (CuAAC). A variety of ligands were synthesized to probe the steric and electronic demands required for use in the CuAAC reaction. Substituents on the 1,2,4-triazine were systematically altered and the core 1,2,4-triazine modified to determine the most active ligand. Additional experiments explored the variability in the reaction conditions, such as solvent choice, use of reducing agents, and optimal stoichiometry. Under optimum conditions 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine and ...


Homogeneous And Heterogeneous Approaches To 1,2,4-Triazine-Accelerated Copper-Catalyzed Azide-Alkyne Cycloadditions, Ashleigh Lauren Prince Aug 2011

Homogeneous And Heterogeneous Approaches To 1,2,4-Triazine-Accelerated Copper-Catalyzed Azide-Alkyne Cycloadditions, Ashleigh Lauren Prince

Doctoral Dissertations

Over the last decade, the domain of click chemistry has grown exponentially and has significantly impacted the fields of organic synthesis, medicinal chemistry, molecular biology, and materials science. The ideal model of a click reaction has become the copper-catalyzed azide-alkyne cycloaddition (CuAAC). Inherent limitations of CuAAC, including high temperatures, long reaction times, and difficult purifications, have been minimized by the development of nitrogen-based ligands. Herein, we present a novel application of 1,2,4-triazines by investigating their use as accelerants for CuAAC.

A diverse library of 1,2,4-triazines were synthesized in order to examine the molecular determinants of their ...


Ticl(Oipr)3-Mediated One-Pot Reductive Amination Of 1,1'-Diacetylferrocene With Aryl Amines, Md Wasi Ahmad, Sang Yeon Lee, Tae Jeong Kim, Hong Seok Kim Dec 2010

Ticl(Oipr)3-Mediated One-Pot Reductive Amination Of 1,1'-Diacetylferrocene With Aryl Amines, Md Wasi Ahmad, Sang Yeon Lee, Tae Jeong Kim, Hong Seok Kim

Dr. Mohammad Wasi Ahmad (Md Wasi Ahmad)

No abstract provided.


Method For Direct Preparation For 1,2,4-Triazole From Hydrazine And Formamide, Harris E. Petree, Joseph R. Pociask, John T. Gupton Jan 1981

Method For Direct Preparation For 1,2,4-Triazole From Hydrazine And Formamide, Harris E. Petree, Joseph R. Pociask, John T. Gupton

Chemistry Faculty Publications

Process for the preparation of 1,2,4-triazole comprises contacting hydrazine or its aqueous solutions with at least about 2.5 moles of formamide at a temperature of 140° to 210° C. and then recovering the resultant 1,2,4- triazole in yields of 92-98% with 94-98% purity. The formamide is maintained in an excess over about the 2.5 molar amount consumed in the reaction with the hydrazine. Recovery steps for isolating the 1,2,4-triazole are disclosed.