Practical Aspects of Combinatorial Solid‐Phase Synthesis

Hlaváč, Jan; Soural, Miroslav; Krchňák, Viktor

doi:10.1002/9781118141649.ch3

Cited by 11 publications

(5 citation statements)

References 149 publications

(129 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The key advantage of SPS is that all reaction intermediates within the reaction sequence are quickly and simply isolated using filtration and wash with the fresh solvent; thus, parallel synthesis can be easily performed with only simple instrumentation and minimum hands-on time. Consequently, SPS has been frequently applied in pharmaceutical industry to produce collections of compounds for the high-throughput screening to accelerate the process of drug discovery and development …”

Section: Introductionmentioning

confidence: 80%

Synthesis of Polysubstituted Pyridines and Pyrazines via Truce–Smiles Rearrangement of Amino Acid-Based 4-Nitrobenzenesulfonamides

2023

Self Cite

View full text Add to dashboard Cite

Immobilized l-glutamic acid β-methyl ester was sulfonylated with 4-nitrobenzenesulfonyl chloride and alkylated with various α-haloketones. The resulting sulfonamides were reacted with potassium trimethylsilanolate. Then, upon cleavage from the polymer support, tetrasubstituted pyridines were produced as the result of one-step C-arylation, aldol condensation, and oxidation. When cleavage from the resin occurred before the trimethylsilanolate treatment, C-arylation was followed by enamination, which yielded trisubstituted pyrazines. Through the developed protocols, targeted synthesis of novel heterocyclic derivatives was performed using mild reaction conditions and a number of readily available starting materials.

show abstract

Section: Introductionmentioning

confidence: 80%

Synthesis of Polysubstituted Pyridines and Pyrazines via Truce–Smiles Rearrangement of Amino Acid-Based 4-Nitrobenzenesulfonamides

2023

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the late nineties, the Merrifield synthesis on a polymer support 2 expanded from the field of peptides and oligonucleotides to the area of small molecules. With respect to its significant advantages, particularly the simple isolation of reaction intermediates and quick production of chemical libraries, 3 the solid-phase synthesis (SPS) of heterocycles was extensively studied during the first decade of the new millennium. Recently, considerable attention was paid to the application of SPS to the chemistry of α-haloketones to prepare various five-to seven-membered scaffolds.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Solid-Phase Synthesis of Heterocycles with α-Haloketones as the Key Building Blocks

Fülöpová

Soural

2016

Synthesis

Self Cite

View full text Add to dashboard Cite

This short review summarizes the use of α-haloketones in the preparation of various heterocycles with the application of solidphase synthesis. A literature survey revealed that eighteen different five-to-seven membered scaffolds are accessible, including condensed heterocycles and bisheterocycles. 22 Conclusion Key words α-haloketones, heterocycles, rearrangement, solid-phase synthesis, cyclization Miroslav Soural (left) was born in Olomouc, Czech Republic, in 1978. He studied chemistry at Palacky University, Olomouc, where he also received his Ph.D. in organic chemistry (in 2006). After his postdoctoral fellowship at the University of Notre Dame (USA), he was appointed Associated Professor at Palacky University, Olomouc. From 2012 he has held the position of Senior Researcher at the Institute of Molecular and Translational Medicine. His field of interest is the development of strategies for the solid-phase synthesis of various pharmacologically promising substances with the emphasis on heterocyclic chemistry. Veronika Fülöpová (right) was born in Opava, Czech Republic, in 1985. During her graduate studies at Palacky University, Olomouc (Czech Republic) she became an investigator on several student grant projects regarding the solid-phase synthesis of novel heterocyclic compounds. After defending her Ph.D. thesis devoted to nitrobenzenesulfonamide chemistry, she received her Ph.D. degree in 2015 from the same university. Currently, she is working as a researcher at the Institute of Molecular and Translational Medicine in Olomouc, and the main area of her interest is solution-/solid-phase synthesis of nitrogenous heterocycles with potential biological activity.

show abstract

“…The most apparent benefits are facilitated washing of the reagents and isolating of the target products, and the ability to carry out parallel syntheses to produce large libraries containing thousands of compounds intended for biological screening. The practical aspects of combinatorial solid-phase organic synthesis were summarized [66].…”

Section: Introductionmentioning

confidence: 99%

Isocyanide Multicomponent Reactions on Solid Phase: State of the Art and Future Application

Cankařová

Krchňák

2020

IJMS

Self Cite

View full text Add to dashboard Cite

Drug discovery efforts largely depend on access to structural diversity. Multicomponent reactions allow for time-efficient chemical transformations and provide advanced intermediates with three or four points of diversification for further expansion to a structural variety of organic molecules. This review is aimed at solid-phase syntheses of small molecules involving isocyanide-based multicomponent reactions. The majority of all reported syntheses employ the Ugi four-component reaction. The review also covers the Passerini and Groebke-Blackburn-Bienaymé reactions. To date, the main advantages of the solid-phase approach are the ability to prepare chemical libraries intended for biological screening and elimination of the isocyanide odor. However, the potential of multicomponent reactions has not been fully exploited. The unexplored avenues of these reactions, including chiral frameworks, DNA-encoded libraries, eco-friendly synthesis, and chiral auxiliary reactions, are briefly outlined.

show abstract

Practical Aspects of Combinatorial Solid‐Phase Synthesis

Cited by 11 publications

References 149 publications

Synthesis of Polysubstituted Pyridines and Pyrazines via Truce–Smiles Rearrangement of Amino Acid-Based 4-Nitrobenzenesulfonamides

Synthesis of Polysubstituted Pyridines and Pyrazines via Truce–Smiles Rearrangement of Amino Acid-Based 4-Nitrobenzenesulfonamides

Solid-Phase Synthesis of Heterocycles with α-Haloketones as the Key Building Blocks

Isocyanide Multicomponent Reactions on Solid Phase: State of the Art and Future Application

Contact Info

Product

Resources

About