Solid-Phase Synthesis of Trisubstituted 2,5-Dihydrobenzo[<i>f</i>][1,2,5]thiadiazepine 1,1-Dioxide Derivatives

Fülöpová, Veronika; Krchňák, Viktor

doi:10.1021/co500084k

Cited by 17 publications

(5 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the case of intermediates 74, prepared from immobilized serine, the cleavage procedure resulted in the formation of morpholine derivatives 77 (Scheme 15). 1b, 20 The same reaction course was observed after reduction of the nitro group, which showed the predominant formation of the six-membered scaffold 78. Formation of dihydrobenzothiadiazepine 1,1-dioxide 71 from the intermediate 76 was not observed.…”

Section: Morpholines: Path Bmentioning

confidence: 54%

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

Section: Morpholines: Path Bmentioning

confidence: 54%

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

show abstract

“…After reduction of the nitro derivative 161, the seven-membered scaffold was spontaneously formed on the resin, and the final acid-mediated cleavage afforded the target benzodiazepines 162 (Scheme 28). The use of 2-nitrobenzenesulfonyl chlorides (2-Nos-Cls) resulted in intermediate 159 with the nitro group in the o-position, and then, reduction and cyclization afforded the corresponding benzothiadiazepine 1,1-dioxide derivatives [61]. Furthermore, employing 2-Nos-Cls and benzothiadiazepine 1,1-dioxides was recently obtained from polymer-supported α-amino acids using alcohols as the building blocks for the Fukuyma-Mitsunobu N 2 -alkylation [62].…”

Section: Pyrrolobenzodiazepinesmentioning

confidence: 99%

Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms

Fülöpová

Soural

2017

Topics in Heterocyclic Chemistry

Self Cite

View full text Add to dashboard Cite

Due to the importance of diazepines and diazepanes in medicinal chemistry and chemical biology, their preparation from diverse starting materials has been frequently reported. In this chapter, we summarize all strategies employing the method of solid-phase synthesis. More than seventeen different types of target compounds are accessible. The individual approaches are grouped according to the type of the target scaffold.

show abstract

“…The reaction of polymer-supported 2- or 4-nitrobenzensulfonamides with α -haloketones allows the simple production of many different heterocycles using the concept of diversity-oriented synthesis [ 1 ]. Recently, this chemistry was used to prepare morpholines and thiomorpholines from polymer-supported serine and cysteine via the corresponding α -acylamino ketones [ 2 , 3 , 4 ]. In addition, fused benzodiazepine-oxazines I , II [7 + 6] or pyrazino-oxazines III [6 + 6] were obtained via the acylation or sulfonylation of α -acylamino ketones with different reagents (see Scheme 1 ) [ 5 , 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Convenient Synthesis of Thiohydantoins, Imidazole-2-thiones and Imidazo[2,1-b]thiazol-4-iums from Polymer-Supported α-Acylamino Ketones

et al. 2018

View full text Add to dashboard Cite

The preparation of 5-methylene-thiohydantoins using solid-phase synthesis is reported in this paper. After sulfonylation of immobilized Ser (t-Bu)-OH with 4-nitrobenzenesulfonyl chloride followed by alkylation with various bromoketones, the 4-Nos group was removed and the resulting polymer-supported α-acylamino ketones reacted with Fmoc-isothiocyanate. Cleavage of the Fmoc protecting group was followed by the spontaneous cyclative cleavage releasing the 5-methylene-thiohydantoin derivatives from the polymer support. Reduction with triethylsilane (TES) yielded the corresponding 5-methyl-thiohydantoins. When Fmoc-isothiocyanate was replaced with alkyl isothiocyanates, the trifluoroacetic acid (TFA) mediated cleavage from the polymer support, which was followed by the cyclization reaction and the imidazo[2,1-b]thiazol-4-iums were obtained. Their conversion in deuterated dimethylsulfoxide led to imidazole-2-thiones.

show abstract

Solid-Phase Synthesis of Trisubstituted 2,5-Dihydrobenzo[f][1,2,5]thiadiazepine 1,1-Dioxide Derivatives

Cited by 17 publications

References 30 publications

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

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

Solid-Phase Synthesis of Seven-Membered Heterocycles with Two Nitrogen Atoms

Convenient Synthesis of Thiohydantoins, Imidazole-2-thiones and Imidazo[2,1-b]thiazol-4-iums from Polymer-Supported α-Acylamino Ketones

Contact Info

Product

Resources

About