C–C Bond Cleavage of Keto-Aziridines; Synthesis of Oxazoles <i>via</i> Regio-Controlled Ring Expansion

Samimi, Heshmat Allah; Entezami, Soraya

doi:10.3184/174751913x13843364573005

Cited by 6 publications

(2 citation statements)

References 36 publications

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“…Derivatives of oxadiazole-2-tines are of undoubted interest in the search for new antibacterial drugs, since they contain a number of pharmacophore groups [14][15][16]. In this regard, in order to search for new anti-tuberculosis drugs and study the structure-activity relationship [17][18][19][20][21], we studied the interaction of acylglycine hydrazides with carbon disulfide in the presence of potassium hydroxide. Further acidification of the resulting potassium salt of dithiocarbamic acid with 0.1 N HCl solution leads to the formation of cyclic products -1,3,4-oxadiazole-2-thiones.…”

Section: Some Directions In the Modification Of Azolesmentioning

confidence: 99%

Some Directions in the Modification of Azoles

Ibrayev¹,

Takibayeva²,

Фазылов³

et al. 2020

OF THE ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN

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This article presents studies on the targeted search for new derivatives of azoles, such as benzthiazole, 3,5-dimethylpyrazole, 1,3,4-oxadiazole-2-thione, 1,3,4-thiadiazole. The possibility of combining in one molecule of the azole ring with other cyclic compounds: the alkaloid cytisine, morpholine, furan and some arenes has been studied. To obtain new compounds, the reactions of bromination, acylation, and interaction with isothiocyanates were studied. Optimal synthesis conditions were studied for all reactions. It was found that the reaction of 4-bromo-3,5-dimethylpyrazole with isothiocyanates, in contrast to the previously written derivatives of anilines, takes a longer time and requires heating the reaction mixture. The combination of a pirasol fragment with halide substituents often results in an enhanced therapeutic effect. The synthesized 2-bromine-N-(6-rodanbenzo[d]thiazole-2-yl)acetamide, due to the alkylbromide group, is an important synth in the synthesis of new benzthiazole derivatives. Its derivatives combine in one molecule the rest of rhodanbenzthiazole with alkaloid cytisine and biogenic amine morpholine and are potentially biologically active compounds, since the molecule structure contains several pharmacophoric fragments: benzthiazole and alkaloid (amine) heterocycles, rhodane and urea groups. The mechanism of formation of 1,3,4-oxadiazole-2-tyons from hydrazides under action on them by carbon disulfide was studied and assumed. It was shown that dithiocarbamates in acidic medium decompose with the release of hydrogen sulfide and the formation of highly reactive isothiocyanate group. Then, intra-molecular cyclization occurs, with the formation of end products - 1,3,4-oxadiazole-2-thions. The structures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy. All synthesized substances are potentially biologically active compounds, since they contain several pharmacophore fragments in their structure.

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Section: Some Directions In the Modification Of Azolesmentioning

confidence: 99%

Some Directions in the Modification of Azoles

Ibrayev¹,

Takibayeva²,

Фазылов³

et al. 2020

OF THE ACADEMY OF SCIENCES OF THE REPUBLIC OF KAZAKHSTAN

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“…10 A successful utilization of iodine in refluxing dimethyl sulfoxide was also shown for this transformation. 11 Coordination of iodine to the nitrogen atom is proposed to induce a C-C bond ring opening of aziridines 21 followed by 1,5-electrocyclization. Electrondeficient aziridines (R 1 = 3-NO 2 C 6 H 4 , R 2 = Ph, 4-ClC 6 H 4 ) were not involved in this transformation and suffered from side reactions, in particular, hydrolysis by residual water in DMSO to produce 3-nitrobenzaldehyde.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in the Chemistry of 2-Acylaziridines

Pankova

Кузнецов

2017

Synthesis

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This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.1 Introduction2 Reactions via C–C Bond Cleavage3 Reactions via C–N Bond Cleavage3.1 Reactions Starting with the Aziridine Ring Opening3.2 Reactions Starting at the Carbonyl Group4 Conclusion

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Molecular Rearrangements

Coxon¹

2016

Organic Reaction Mechanisms · 2013

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C–C Bond Cleavage of Keto-Aziridines; Synthesis of Oxazoles via Regio-Controlled Ring Expansion

Abstract: The ring expansion of keto-aziridines to the corresponding 2,5-diaryloxazoles in the presence of iodine in refluxing dimethyl sulfoxide, is described. A plausible mechanism for the synthesis of 2,5-diaryloxazoles is proposed.

Cited by 6 publications

References 36 publications

Some Directions in the Modification of Azoles

Some Directions in the Modification of Azoles

Recent Advances in the Chemistry of 2-Acylaziridines

Molecular Rearrangements

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