Asymmetric organocatalytic sulfa-michael reactions of thioglycolate with isatin derived nitroalkenes

Download

index.pdf

Date

2018

Author

Sağesen, Selin

Metadata

Show full item record

Item Usage Stats

306
views

100
downloads

Organosulfur compounds are present in many natural products and drugs. Sulfa-Michael reaction is the prominent method to synthesize these molecules. The novel bifuctional organocatalysts developed in our research group enable sulfa-Michael reaction to ocur asymmetrically. In this thesis, biologically active isatin derived nitroalkenes were chosen as Sulfa-Michael acceptors. Addition of methyl thioglycolate to isatin derived nitroalkenes in the presence of the bifunctional organocatalysts was studied under different conditions. Solvent, temperature, catalyst loading and concentration screenings were done. Isatin derived nitroalkenes substituted from different positions were also tested in sulfa-Michael reactions under optimized conditions. Sulfa-Michael product was synthesized with 75% yield and 70% ee when 10 mol % 1-adamantyl squaramide/quinine catalyst was used. The nitro group in the structure was reduced catalytically in order to reveal the product to be utilized in further reactions.

Subject Keywords

Organosulfur compounds., Asymmetric synthesis., Thioglycolic acid., Nitroalkenes., Isatin.

URI

http://etd.lib.metu.edu.tr/upload/12622794/index.pdf
https://hdl.handle.net/11511/27685

Collections

Graduate School of Natural and Applied Sciences, Thesis

Suggestions

OpenMETU
Core

Bioactive thiazole and benzothiazole derivatives Rouf, Abdul; Tanyeli, Cihangir (2015-06-05) The heterocycles are the versatile compounds existing in almost all natural products and synthetic organic compounds, usually associated with one or the other biological activity. Among the heterocycles the thiazoles and benzothiazoles occupy a prominent position. They possess a broad range of biological activities and are found in many potent biologically active molecules and drugs such as vitamin thiamine, sulfathiazol (antimicrobial drug), ritonavir (antiretroviral drug), abafungin (antifungal drug) and ...
Synthesis of alkynyl-substituted pyrrole and 1,4-thiazepine derivatives Yılmaz, Elif Serel; Zora, Metin; Department of Chemistry (2018) Heterocyclic compounds have a great importance in medicinal chemistry because of their presence in a number of pharmaceuticals. Among them, pyrroles and 1,4-thiazepines play a vital role in pharmaceutical chemistry because of their presence in a number of bioactive molecules and natural products. For this reason, the development of new synthetic methods for the synthesis of these compounds has attracted much attention. Recently, the cyclization of functionally-substituted alkynes has emerged as a valuable t...
Enzymatic hydrolysis by transition-metal-dependent nucleophilic aromatic substitution Kalyoncu, Sibel; Heaner, David P.; Kurt, Zöhre; Bethel, Casey M.; Ukachukwu, Chiamaka U.; Chakravarthy, Srinivas; Spain, Jim C.; Lieberman, Raquel L. (2016-12-01) Nitroaromatic compounds are typically toxic and resistant to degradation. Bradyrhizobium species strain JS329 metabolizes 5-nitroanthranilic acid (5NAA), which is a molecule secreted by Streptomyces scabies, the plant pathogen responsible for potato scab. The first biodegradation enzyme is 5NAA-aminohydrolase (5NAA-A), a metalloprotease family member that converts 5NAA to 5-nitrosalicylic acid. We characterized 5NAA-A biochemically and obtained snapshots of its mechanism. 5NAA-A, an octamer that can use sev...
Resveratrol as a Growth Substrate for Bacteria from the Rhizosphere Kurt, Zöhre; Spain, Jim C. (2018-05-01) Resveratrol is among the best-known secondary plant metabolites because of its antioxidant, anti-inflammatory, and anticancer properties. It also is an important allelopathic chemical widely credited with the protection of plants from pathogens. The ecological role of resveratrol in natural habitats is difficult to establish rigorously, because it does not seem to accumulate outside plant tissue. It is likely that bacterial degradation plays a key role in determining the persistence, and thus the ecological...
Biological Treatment of Micropollutants Bayramoğlu, Tuba Hande (IWA Publishing, 2010-01-01) Municipal wastewater is the main source of micropollutants which are present in the household products (detergents, cosmetics and paints) and natural excretion of humans (drugs and metabolites, synthetic hormones) (Bruchet et al., 2002; Bicchi et al., 2009). After their use, pharmaceuticals are excreted intact and/or as metabolites with feces and urine; thus are introduced directly into wastewater (Lo¨ffler et al., 2005). New sanitation concepts where wastewater streams are separated and treated according t...

Citation Formats

S. Sağesen, “Asymmetric organocatalytic sulfa-michael reactions of thioglycolate with isatin derived nitroalkenes,” M.S. - Master of Science, Middle East Technical University, 2018.