Organic Chemistry Commons^™

Catalytic Synthesis Of Protoberberine Alkaloids And Their Evaluation As Selective Dopamine Receptor Ligands, Ashok Reddy Gudipally

Dissertations, Theses, and Capstone Projects

Dopamine regulates motor control, cognition, reward, motivation, and neuroendocrine signaling. Disruption of dopaminergic neurotransmission is closely linked to central nervous system disorders, including Parkinson’s disease, schizophrenia, addiction, and related neuropsychiatric conditions. Because these functions are mediated by multiple dopamine receptor subtypes with distinct roles in physiology and disease, the discovery of subtype-selective ligands remains an important goal in neuropharmacology. Within this context, protoberberine alkaloids, particularly tetrahydroprotoberberines (THPBs), are attractive molecular frameworks because they combine structural complexity with broad biological relevance, including measurable activity in CNS-related diseases. Prior work from our laboratory and others established (–)-stepholidine (1.60) as an important lead …

Multicomponent Reaction-Initiated Synthesis Of Polyheterocyclic Compounds, Ashutosh Nath

Graduate Doctoral Dissertations

Efficient synthesis of novel heterocycles with biological interest remains a challenge in modern organic chemistry. This dissertation presents the development of efficient synthetic strategies that combine multicomponent reactions (MCRs) with sequential reactions for rapid access a diverse array of polyheterocyclic compounds. The projects are: 1) Groebke-Blackburn-Bienaymé (GBB) reaction followed by N-acylation and Friedel-Crafts (FC) cyclization for the construction of imidazopyridine- and indole-fused azepinones involving an unusual ring-expansion process. 2) Modified GBB condensation products for intramolecular Diels-Alder (IMDA) cycloaddition and dehydrative re-aromatization to access imidazopyridine-fused isoquinolinones. 3) Integration of the Ugi-three component reaction (Ugi-3CR) and Pictet-Spengler (PS) reaction followed by …

Techniques, Skills, And Synthesis For “Cooking” In The Organic Laboratory, Emily C. Sylvester, Tim Evans

Open Education Materials

Lab manual for CHEM 211L, Organic Chemistry I Laboratory. Provides background and procedures for laboratory experiments, including fundamental techniques and several organic syntheses.

Creative Commons attribution.

Isolation Of Lavender Compounds Via Steam Distillation, Emma Norris, Gwendolyn Flippin

Discovery Day - Daytona Beach

Steam distillation was used to extract (R)- Linalool, Linalyl acetate, and Camphor from lavender during the steam distillation experiment. The compounds were extracted via a steam distillation apparatus. A 250 mL two-neck round-bottom flask, a thermometer adapter, 25 mL a thermometer, a condenser, a distillation head, a vacuum adapter, lab jacks, and clamps made up the apparatus. Then the lavender was massed out and added to a beaker with 100 mL of water. Over time, the distillate is collected in a vial to be analyzed. (R)- Linalool is a nonaromatic alcohol containing two alkenes with the chemical formula C_10 H_18 …

Chemical Profiling Of Star Anise (Illicium Verum) Via Gc–Ms: Identifying Compounds With Pharmaceutical Potential, Legacy Wilson, Yegor Bushnev

Discovery Day - Daytona Beach

Title: Chemical Profiling of Star Anise (Illicium verum) via GC–MS: Identifying Compounds with Pharmaceutical Potential   Abstract: Star anise (Illicium verum) has been used for both medicinal and culinary applications due to its diverse bioactive compounds. It is a primary natural source of shikimic acid (𝐶7𝐻10𝑂5), a key precursor in the synthesis of the antiviral drug oseltamivir (Tamiflu), used to treat influenza. Additionally, star anise has been used to treat respiratory and digestive conditions and is widely used for flavoring due to its licorice-like aroma, mainly from trans-anethole (𝐶10𝐻12𝑂) , its major component. Previous studies have also demonstrated mild central nervous …

Extracting Aromatic Compounds From Dehydrated Rose Buds, Lana Sheridan

Discovery Day - Daytona Beach

Eugenol (C10H12O2), methyl eugenol (C11H14O2), and 2-phenylethanol (C8H10O) are chemically aromatic, natural compounds commonly present in various botanical sources and essential oils. Structurally, eugenol is a methoxyphenol bearing an allyl side chain; its methyl ether derivative, methyl eugenol, shares a similar framework but features a methoxy group replacing the free phenolic hydroxyl group found in eugenol. 2-Phenylethanol is an aromatic alcohol comprised of a benzene ring linked to an ethanol moiety. The objective of this project was to isolate and characterize these compounds in dried rose buds using distillation followed by chromatographic and spectrometric analysis. For the experiment, a steam …

Steam Distillation Star Anise, Makayla Maso, Kiara Maso

Discovery Day - Daytona Beach

Star anise (Illicium verum) contains several volatile organic compounds responsible for its characteristic aroma, including trans-anethole, estragole, limonene, and linalool. These compounds differ in structure and chemical properties, which influence their behavior during isolation and analysis. Trans-anethole and estragole are classified as aromatic phenylpropene derivatives that contain benzene rings and ether functionalities. In contrast, limonene and linalool are non-aromatic terpenes, with linalool additionally possessing an alcohol functional group. These compounds are widely utilized as flavoring agents and fragrance components, while terpenes such as limonene and linalool are also commonly employed as solvents and in formulation chemistry due to their volatility …

Extraction Of Cedarwood Essential Oils Via Steam Distillation, Forrest Dohner

Discovery Day - Daytona Beach

Many natural materials, including pine and eucalyptus, produce distinct scents due to the presence of volatile organic compounds. In cedarwood, this aroma arises from a combination of aromatic molecules, which are organic compounds containing conjugated carbon ring systems that interact with olfactory receptors. Specifically, cedarwood contains three primary compounds responsible for its scent: cedrol, cedrene, and thujopene. The objective of this experiment was to extract these essential oils from cedarwood and identify their chemical composition. Steam distillation was used to isolate the volatile components by passing steam through the cedarwood, causing the essential oils to vaporize at temperatures below their …

Production And Analysis Of Lavender Essential Oil: Extraction, Composition, And Applications, Mary Zoeller

Discovery Day - Daytona Beach

Steam distillation was performed to extract essential oil from lavender and analyze its chemical composition. Lavender is known to contain several compounds such as linalool, terpinen-4-ol, and linalyl acetate, which contribute to its characteristic aroma and biological activity. The purpose of this experiment was to isolate these compounds without decomposition and identify them using gas chromatography–mass spectrometry (GC-MS). Approximately 14.851 g of lavender was heated with water to generate steam, which carried the volatile compounds into a condenser where the vapor was cooled and collected. The distillate was transferred to a separatory funnel to isolate the organic layer from the …

Steam Distillation Of Jasmine, Mikayla Hulvey, Meliah Martin

Discovery Day - Daytona Beach

This experiment aimed to isolate various components, including benzyl acetate, linalool, indole, and farnesene, from jasmine buds. The functional groups include an ester in benzyl acetate, an alcohol in linalool, an amine in indole, and alkenes in farnesene. Jasmine buds were combined with distilled water and steam distilled using a standard distillation apparatus. The distillate, containing hydrosol and trace amounts of essential oil, was then collected for extraction using methyl tert-butyl (MTBE) for a liquid-liquid extraction. The organic layer was then separated, washed using brine, dried over anhydrous sodium sulfate, and then transferred for later analysis. The essential oil obtained …

Developing Solvent Tolerant Microbial Membranes: Lipid Extraction And Laurdan Fluorescence Approaches For Biofuel Optimization, Gladstone Anku

Electronic Theses and Dissertations

The high demand for sustainable energy has increased interest in advanced biofuels, though production is limited by solvent toxicity to microbial hosts. This study investigated the role of lipid composition in modulating membrane fluidity and solvent tolerance using Bacillus subtilis as a model organism. Five strains were cultured, and membrane lipids were extracted and analyzed using thin-layer chromatography and gas chromatography–mass spectrometry; however, inconsistent results limited compositional characterization. To address this problem, reconstituted vesicles composed of phosphatidylglycerol (PG) and phosphatidylethanolamine (PE) were used as model membranes. Membrane fluidity was assessed using Laurdan fluorescence spectroscopy by measuring generalized polarization (GP) values …

Solvent-Free Ball-Milling Synthesis Of 1,2-Disubstituted Benzimidazoles, Zachary A. Jaffery, Katherine E. Christopher, Kyle A. Grice

DePaul Discoveries

The search for sustainability in chemistry has led to the development of the field of Green Chemistry, comprised by 12 guiding principles. Existing syntheses of benzimidazoles, a heterocycle widely used in medicinal chemistry, utilize methods with much room for improved sustainability. This work presents a solventless mechanochemical synthesis of 1,2-disubsituted substituted benzimidazoles from the condensation of phenylenediamines and aryl aldehydes. The effect of milling aid on yield and selectivity was investigated and montmorillonite K10 was determined to be the best milling aid. The purification protocol was optimized as well, with a heptane:EtOAc extraction and subsequent recrystallization from EtOH found to …

Recent Advances In Phosphatidylinositol Phosphate Kinases (Pipks) And Their Inhibitors, Mengxia Sun, Jian Hu, Xuefei Huang

BAU Journal - Science and Technology

Phosphatidylinositol phosphate kinases (PIPKs) are an important class of enzymes in humans, which produce lipid signaling molecules playing central roles in pathogenesis of diseases such as cancer, neurodegenerative diseases, and viral infection. Consequently, they are attracting increasing attention as drug targets for disease treatment. This review summarizes the functions of the PIPK family enzymes and highlights recent efforts on designing novel inhibitors against PIPKs. These advances are extensively discussed to stimulate interest in this field and promote further development of highly potent and selective inhibitors for innovative therapeutic applications.

Regioselective Tellurination Reactions And Their Utilities, Itunu Comfort Olanrewaju

Masters Theses

This thesis provides a comprehensive study of regioselective tellurination and its applications by integrating experimental and computational techniques, with an aim of synthesizing libraries of organotellurium heterocycles. This study addresses existing challenges in regioselective tellurination, such as unpredictable regioselectivity and avoidance of toxic reagents by harnessing intramolecular Te…O coordination and electrophilic aromatic tellurination. This strategy enables the development of previously poorly accessible compounds including benzotellurazinones, 2-acylaminobenzotellurazoles, and previously unknown 2,3-dihydrobenzo [b] oxatelluranes, which were prepared by antiMarkovnikov anti-addition of TeCl4 to C-C triple bonds. Experimental studies were complemented by computational DFT analyses to provide mechanistic and energetic insight into the …

Biomedical Applications Of Structurally Defined Natural And Semi-Synthetic Saponins, Chaeeun Lim-Paik

ETDs from 2020-2029

Triterpenoid saponins are amphiphilic glycosides that exhibit a wide range of biological and pharmacological properties, including antifungal, antiviral, molluscicidal, hypoglycemic, and hypocholesterolemic effects. These biological and pharmacological properties make saponins attractive for diverse applications. In this work, we demonstrate three biological applications: (i) immunostimulant vaccine adjuvant, (ii) protein delivery enhancement, and (iii) gene transfection enhancement. In light of the strong structure dependence of saponin activity, expanding the structural diversity of available scaffolds is essential for establishing structure-activity relationships (SAR) across these applications. Here, we expanded our saponin collection through semi-synthetic derivatization and the isolation of new saponins from distinct natural …

Oer Organic Chemistry I Lab Manual, Ji Kim

Open Educational Resources

This Organic Chemistry I Lab Manual presents ten inquiry-based modules that integrate green chemistry principles into every stage of the microscale laboratory experience. Students use Kontes microscale glassware to perform essential techniques, including distillation, recrystallization, extraction, chromatography, and nucleophilic substitution reactions. Each module features standardized learning objectives, pre-lab questions, microscale procedures, data tables, and post-lab analysis. Green Chemistry Connections explicitly links each experiment to the Twelve Principles, emphasizing waste prevention, safer solvents, renewable feedstocks, and accident reduction. From isolating caffeine from tea and lycopene from tomato paste to synthesizing cyclohexene via E1 elimination, students learn classical organic chemistry through an …

Computer-Aided Development Of Novel Antioxidants, Rita Bernadett Vlocsko

Graduate Doctoral Dissertations

Physiological redox homeostasis is a fine balance between prooxidants and antioxidants that are integrated elements of several reduction-oxidation mechanisms at molecular, organellar, cellular and tissue levels. When this equilibrium is disrupted and prooxidants become dominant, the body relies on endogenous and exogenous antioxidants to counterbalance the dysregulation and ultimately prevent the progression of oxidative stress. Reactive species (reactive oxygen species, reactive nitrogen species, or reactive sulfur species) are significant contributors to prooxidant activity. Over the years, substantial knowledge has been accumulated regarding their origin and roles in disease development, leading to the discovery and development of antioxidants that effectively target …

Du Undergraduate Showcase Abstracts: Research, Scholarship, And Creative Works, Sophia Wismar, Henry Staats, Allison Metzler, Chloe Puckett, Rachel Levine, Christa Kilpatrick, Scott Wolf, Joe Walsh, Grace Doolittle, John Engebreston, Zoe Lopez, Christopher Aaby, Audrey Duff, Timothy Sisk, Katelyn Lamberton, Angela Narayan, Gilkah Argueta, Habiba Samir, Girena Tesfazghi, Genet Kenore, Sinit Tesfamariam, Effley Brooks, Abi Newell, Megan Doherty, Natalie Baer, Lexi Blood, Talya Riciputi, Jessica Jimenez, Devin Hernandez, Lynn Clark, Taj Kumar, Sunil Kumar, Allen Rutman, Mira Pronobis, Tess Carson, Anna Sher, Frankie Stroud, Tamra Pearson D'Estree, Alyssa Wilson, Emily Melnick, Jenalee Doom, Yihang Gao, Gwendolyn Geiger, Noah Gettle, Scott Nichols, Clare Ayoub, Cara Dienno, Sunny Walker, Zoe Hansen, Maya Wheeler, Addison Rice, Patrick Martin, Sanjana Acharya, Daniel Mcintosh, Amanda Mckellips, Calli Cain, Justin Blake, Peter Sokol-Hessner, Natalie Miller, Max Weisbuch, Sophia Dellota, John Macikas, Charlotte Snow, Mark Siemens, Zoe Lynch, Alex Huffman, Prachi Shah, Jason Roney, Halcyon Levi, Nicole Herzog, Andrea Koly, Daniel Linseman, Annie London, Xi Yang, Avery Zwisler, Jane Smith, Chaz Contag, Michael Kerwin, Lucy Rand, Grace Schroeder, Michelle Rozenman, Nissa Tapper, Guiming Zhang, Mateo Mazariego-Halpern, Keith Meyer, Julie Do, Dakota Park-Ozee, Travis Herink, Kara Neu, Jonathan Plomin, Eve-Odine Duchaufour, Debbie Gale Mitchell, Tennyson Anderson-Stricklin, Lily Treitz, Samantha Rosenberger, Sierra Griffith, Finley Joseph, Daniel Sampson, Emmy Davis, Skyler Kasnoff, Evon Lopez, Vivian Nguyen, Cassy Young, Franklin Sellner, Martin Tobon, Ila Graham, Zach Billings, Holden Hedit, Decatur Boland, Paul Kosempel, Cory Chandler, Jay Mahoney, Sam Dragan, Susan Dagget, Yarrow Ator, Heidi Vuletich, Owen Weber, Andrew Kloeppel, Petersen Gray, Mandi Schaeffer-Fry, Razleen Bassra, Bryanna Rodriguez, Christina Blue, Taubie Sanders, Rachel Epstein, Luke Milburn, Camryn Evans, Ezra Martinez, Mary Westwood, Gabri Notov, Robin Tinghitella, Lilou Cabrol, Eli Barbour, Juliet Mendik, Selma Myers, Zac Wise, Noah Fahlin, Michelle Knowles, Abigail Hopper, Michael Greenberger, Romi Laclair, Sarah Watamura, Sabrina Efroymson, Casey Barker, Sydney Seltzer, Bryn Yehle, Jennifer Hoffman, Sara Garcia, Ryuka Nagamine, Trevor Briggs, Remy Le Boeuf, Elena Krone, Eileen Farrell, Regan O'Rourke, Elena Roel, Greg Mortimer, Ali Ayoub, Stefani Langehennig, Caitlin Turk, Logan Scmid, Stefan Chavez-Norgaard, Karen Kim, Tatiana Peccedi, Courtney Cassidy, John Sebesta, Rhianna Lewis, Janice Bening-Lacek, Vivian Lawless, Mckenna Hanson, Jeffrey Amidon, Riya Joshi, Ram Ambre, Brady Worrell, Perrin Schneider, Ali Azadani, Brooke Agulnek, Lyndsie Salvagio, Elise Siemanowki, Yan Qin, Andre Allen, Melodie Nguyen, Megan Livengood, Abby Reams, Saffron Hartreeve, Bri Wylie, Sarah Brookman, Mariah Loiacono, Green Russo, Abhia Lodhi, Gabrielle Welsh, Nika Spehar, Shahked Levin, Evrim Baykal, Kimberly Chiew, Jocelyn Torres, Kailey Hicks, Mykaela Tanino-Springsteen, Audrey Bellows, Akam Chahal, Madeline Tepper, Shannon Murphy, Alexa Fonseca, Deborah Han, Cassandra Perez, Oluwatoyin Alaba, Julia Roncoroni, Vy Nguyen, Nana Burn, Sarah Sasse, Rubin Tuder, Anthony Gerber, Nancy Lorenzon, Christine Vohwinkel, Camryn Gunter, Tristan Weber, Sam Rommel, Brian Michel, Muskan Fatima, Alannah Oleson, Kira Frey, Edward Garrido, Beckett Morris, Kerstin Haring, Drew Middleton, Abigail Walpert, Liam Dee, Gabby Ishaw, Cole Carnes, Maddie Weiser, Claire Fox, Valeriia Vlasenko, Kateri Mcrae, Riley Smith, Abigail Templin, Kushani Rajapaksha

DU Undergraduate Research Journal Archive

Abstracts from the DU Undergraduate Research Showcase.

Arylation Of Nitrogen, Oxygen And Carbon Nucleophiles By Aryl(Tmp)Iodonium Salts, Joseph Jordan Hatton

Dissertations and Theses

Substituted aromatic rings are present in industry in a plethora of organic molecules such as pharmaceuticals, agrochemicals, materials and beyond. Therefore, methods for broadly installing aryl rings into other compounds to create substituted aromatic rings are valuable to many organic chemists. Historically these transformations are achieved through methods such as nucleophilic aromatic substitution and metal catalyzed cross-coupling. Nucleophilic aromatic substitution is a user-friendly method in this space but is limited by reliance on specific electronics. Metal catalyzed cross-coupling reduced the dependence on electronics in this space, but metals are generally unattractive reagents due to high costs, toxicity and challenges with …

Friedel–Crafts Addition Of 3-Alkylated Indoles To Aldehydes: 2-Hydroxyalkylation Promoted By Trimethylsilyl Trifluoromethanesulfonate, Eric Zhou, Helen Xia, C. Wade Downey

Chemistry Faculty Publications

In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and 2,6-lutidine, 3-alkylated indoles undergo Friedel–Crafts silyloxyalkylation when treated with nonenolizable aldehydes. The reaction is general across a wide range of aromatic aldehydes and tolerates a variety of N-alkylated indoles. Deprotection of the silylated product occurs under standard conditions, and in certain cases the initial TMS-protected product can be isolated in high yield.