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Катаев, В. А.; Спирихин, Л. В.; Khaliullin, A. N.; Gailyunas, I. A.

doi:10.1023/a:1022516824376

Cited by 11 publications

(4 citation statements)

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“…The structure of 6 was confirmed by the direction of its synthesis from compound 5 [39] . 24.8% from 5…”

Section: Derivatives Of 3-aminothietan-2-onementioning

confidence: 98%

“…Alkylation at the nitrogen atom by (chloromethyl)thiirane in an aqueous medium, which takes place with a thiirane-thietane rearrangement, is known for two types of heterocyclic systems-xanthines and benzimidazoles [23]. A derivative of 1-(3-thietanyl)benzimidazole in the form of a mixture of isomers was patented as a compound exhibiting anti-inflammatory activity [24].…”

Section: Thiirane-thietane Rearrangementmentioning

confidence: 99%

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Methods for the synthesis of derivatives of 3-aminothietane (Review)

Butkevich

Соколов

Томашевский

et al. 2007

Chem Heterocycl Compd

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“…The structure of 6 was confirmed by the direction of its synthesis from compound 5 [39] . 24.8% from 5…”

Section: Derivatives Of 3-aminothietan-2-onementioning

confidence: 98%

Section: Thiirane-thietane Rearrangementmentioning

confidence: 99%

Methods for the synthesis of derivatives of 3-aminothietane (Review)

Butkevich

Соколов

Томашевский

et al. 2007

Chem Heterocycl Compd

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“…Benzimidazole (bim) and its derivatives are important heterocyclic compounds, having a wide spectrum of pharmacological activities (Kataev et al, 2002;Valdez et al, 2002). This work forms part of a continuing study on Cu II complexes with benzimidazole (Sieroń et al, 1999(Sieroń et al, , 2002, providing the second example of Cu(bim) 4 coordination.…”

Section: Commentmentioning

confidence: 99%

Tetrakis(1H-benzimidazole-κN³)(sulfato-κO)copper(II) dimethyl sulfoxide solvate

Sieroń

2007

Acta Cryst E

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Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.006 Å Disorder in solvent or counterion R factor = 0.041 wR factor = 0.092 Data-to-parameter ratio = 12.9For details of how these key indicators were automatically derived from the article, see SO, displays a square-pyramidal coordination geometry formed by four benzimidazole ligands and a sulfate anion. The molecules are linked by N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds, forming an extensive two-dimensional network in the ab plane.

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“…More recently, the reaction was successfully expanded to include aromatic nitrogen heterocycles (benzimidazoles [5,6], xanthines [5], triazoles [7]) as nucleophilic partners. In our group, the reactions of (-haloalkyl)thiiranes with N-arylsulfamides [8] and isatins [9] have been demonstrated to provide access to 3-substituted thietanes in satisfactory yields.…”

mentioning

confidence: 99%

Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

Butkevich

Zibinsky

Соколов

et al. 2012

Chem Heterocycl Comp

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Alkylation of N-arylcyanamides with (chloromethyl)thiirane in aqueous alkaline solution provides an easy synthetic approach to N-aryl-N-(thietan-3-yl)cyanamides. Yields vary from 34 to 76% and are lower in the case of electron-deficient aryl substituents. The reaction with phenols containing electronwithdrawing groups results in formation of 3-(aryloxy)thietanes in 19-45% yields.Small molecules comprise a vast majority of successfully designed, tested, and clinically approved drugs [1,2]. Structure-activity relationship practices used in early steps of the molecular design call for a large variety of substituents that one should be able to install onto the desired scaffold for the screening purposes. Therefore, simple and selective methods for the functionalization of organic molecules (as can be illustrated by examples of O-alkylation of phenols and N-acylation and N-sulfonylation of amines) play an important role whenever it is necessary to quickly achieve high molecular diversity or optimize the substrate-target interaction by varying the substitution pattern of the substrate. The absence of transition metal catalyst in such reactions is an additional advantage if bioactivity tests are in view.Small-ring heterocycles provide an attractive extension to the small alkyl and cycloalkyl set of substituents, as the presence of a heteroatom allows for an additional hydrogen bonding or dipole interactions between the substrate molecule and its target. Three-membered heterocycles, such as oxirane or aziridine fragments, often introduce unwanted reactivity because of the possibility of ring-opening reactions resulting in formation of electrophilic species. Four-membered heterocyclic fragments containing one heteroatom are inherently stable but notoriously difficult to synthesize. In this work, a simple and versatile method of introduction of 3-thietanyl substituent is discussed.

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Cited by 11 publications

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Methods for the synthesis of derivatives of 3-aminothietane (Review)

Methods for the synthesis of derivatives of 3-aminothietane (Review)

Tetrakis(1H-benzimidazole-κN³)(sulfato-κO)copper(II) dimethyl sulfoxide solvate

Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

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Untitled

Cited by 11 publications

References 0 publications

Methods for the synthesis of derivatives of 3-aminothietane (Review)

Methods for the synthesis of derivatives of 3-aminothietane (Review)

Tetrakis(1H-benzimidazole-κN3)(sulfato-κO)copper(II) dimethyl sulfoxide solvate

Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

Contact Info

Product

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About

Tetrakis(1H-benzimidazole-κN³)(sulfato-κO)copper(II) dimethyl sulfoxide solvate