Mining the Chemical Space: Application of 2/4-Nitrobenzenesulfonamides in Solid-Phase Synthesis

Fülöpová, Veronika; Soural, Miroslav

doi:10.1021/acscombsci.5b00089

Cited by 21 publications

(6 citation statements)

References 99 publications

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“…After cleavage of the Fmoc‐protecting group, the liberated amino derivative 2 was treated with 4‐nitrobenzenesulfonyl chloride (4‐NsCl) to give intermediate 3 in excellent crude purity of 94 % (calculated from LC–UV traces at 205–400 nm). Subsequent Fukuyama alkylation with various aromatic 2‐bromo ketones (Figure ) yielded the corresponding sulfonamides 4 (R 1 ) in high crude purity (88–94 %, LC–UV traces at 205–400 nm). Unlike the previously reported procedure, we had to increase the concentration of mercaptoethanol/DBU (1,8‐diazabicyclo[5.4.0]undec‐1‐ene) and prolong the reaction time to cleave the 4‐Ns group quantitatively (see the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Disubstituted Pyrazino‐Oxazine Derivatives with Controlled Stereochemistry

2017

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Herein, we report a simple synthesis of disubstituted pyrazino‐oxazines with controlled stereochemistry using readily available building blocks: N‐Fmoc‐protected α‐amino acids and 2‐bromo ketones. The convenient solid‐phase synthesis afforded polymer‐supported derivatives of N‐alkylated N‐acylated tert‐butylserine, which were subjected to spontaneous cyclative cleavage to yield the corresponding pyrazine intermediates. The target 1,7,8,9a‐tetrahydropyrazino[2,1‐c][1,4]oxazine‐6,9‐diones were obtained in two steps by acid‐mediated cleavage of the tert‐butyl group followed by cyclization of the oxazine scaffold.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Disubstituted Pyrazino‐Oxazine Derivatives with Controlled Stereochemistry

2017

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“…After the alkylation, the nosyl (Ns) protecting group is cleaved, releasing the regioselectively monoalkylated amine. 18 In the case of polymer-supported intermediates 62, the acylation with o-nitrobenzoic acids provided resins 63. Reduction of the nitro group led to the formation of the internal nucleophile followed by cyclization which yielded the benzodiazepine derivatives 65 (Scheme 12).…”

Section: Benzodiazepinones: Path Amentioning

confidence: 99%

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

Fülöpová

Soural

2016

Synthesis

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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.

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“…[39][40][41][42] It was previously demonstrated that polymer-supported α-amino acids converted into 2/4-nitrobenzenesulfonamides are an excellent pool for the synthesis of various nitrogenous heterocycles. 43,44 Recently, we focused on the application of amino acids with functionalized side chains, e.g. serine or azidoalanine, which yielded various morpholines 45 or triazolodiazepines, 46,47 respectively.…”

Section: Introductionmentioning

confidence: 99%

Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation

Lemrová

Maloň²,

Soural

2022

Org. Biomol. Chem.

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Mining the Chemical Space: Application of 2/4-Nitrobenzenesulfonamides in Solid-Phase Synthesis

Cited by 21 publications

References 99 publications

Synthesis of Disubstituted Pyrazino‐Oxazine Derivatives with Controlled Stereochemistry

Synthesis of Disubstituted Pyrazino‐Oxazine Derivatives with Controlled Stereochemistry

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

Efficient synthesis of pentasubstituted pyrroles via intramolecular C-arylation

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