Spiroheterocyclization of Pyrrolobenzoxazinetriones under the Action of Thiobenzamide. Synthesis of Spiro[thiazolo-5,2′-pyrroles]

Kobelev, A. I.; Stepanova, E. E.; Дмитриев, М. В.; Денисламова, Е. С.; Масливец, А. Н.

doi:10.1134/s1070428018050159

Cited by 10 publications

(8 citation statements)

References 11 publications

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“…The observed PTRs could have proceed through two alternative pathways (Scheme 9), with the first stage being dissociation of the C spiro –S bond [32] in pseudothiohydantoins PThH , affording intermediate A . Then, A could have further undergone either an intramolecular cyclization by NH attack, forming thiohydantoin ThH (path A), or further dissociation to FPD 1 and thiourea.…”

Section: Resultsmentioning

confidence: 99%

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

Kobelev¹,

Tretyakov²,

Stepanova³

et al. 2019

Beilstein J. Org. Chem.

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A highly divergent synthesis of regioisomeric thiohydantoins and pseudothiohydantoins spiro-fused to a pharmacologically valuable pyrrole-2-one fragment involving the reaction of [e]-fused 1H-pyrrole-2,3-diones with thioureas was developed. The obtained spiro pseudothiohydantoin derivatives were found to undergo a pseudothiohydantoin–thiohydantoin rearrangement. The reactions were shown to proceed under catalyst-free conditions in good yields, and the products were isolated without applying preparative chromatography methods.

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Section: Resultsmentioning

confidence: 99%

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

Kobelev¹,

Tretyakov²,

Stepanova³

et al. 2019

Beilstein J. Org. Chem.

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“…Previously, we reported an efficient catalyst-free synthesis of spiro[thiazolo-5,2'-pyrroles] 1 via interaction of pyrrolobenzoxazinetriones (PBTs) 2 with thiobenzamide (Scheme 2) [17–18].…”

Section: Resultsmentioning

confidence: 99%

“…In continuation of this research [17–18], and in order to extend the scope of the reaction, we attempted to involve the simplest aliphatic thioamide, thioacetamide, in the interaction with PBTs 2 . As a result, we obtained the expected spiro[thiazolo-5,2'-pyrroles] 3 , which were found to exist in a form with an exo -methylene group according to the NMR spectra (Scheme 3) [19].…”

Section: Resultsmentioning

confidence: 99%

“…The formed compound 3 had a strong nucleophilic center – the exo -methylene group, which could attack the other molecule of compound 3 to substitute the S atom and form adduct A . Adduct A underwent a decomposition by releasing a molecule of compound 2 [18]. The formed compound B underwent intramolecular cyclization followed by hydrolysis of the imide group with subsequent decarboxylation and formation of the intermediate C that was oxidized by the air oxygen to form compound 4 .…”

Section: Resultsmentioning

confidence: 99%

“…PBT 2a and thioacetamide (in ratio of 1:1) were kept in acetone for 20 min to afford a solution of compound 3a . To the solution obtained 1 equivalent of either PBT 2f or spiro[thiazolo-5,2'-pyrrole] 1a [18] was added (Scheme 5). When 2a was added, we observed the formation of a mixture of compounds 4a and 4f in a ratio of about 1:1, and in the case of addition of 1a , no cross-product 4f was observed (UPLC–MS).…”

Section: Resultsmentioning

confidence: 99%

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Annulation of 1H-pyrrole-2,3-diones by thioacetamide: an approach to 5-azaisatins

Kobelev

Stepanova

Дмитриев

et al. 2019

Beilstein J. Org. Chem.

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Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking‐based target fishing of 1,4‐benzoxazin‐2‐one derivatives

Stepanova

Balandina

Drobkova

et al. 2020

Archiv der Pharmazie

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Seventeen 1,4‐benzoxazin‐2‐ones bearing the enaminone moiety and three of their analogs were tested for the antibacterial activity against Mycobacterium tuberculosis (H37Rv). Minimal bactericidal concentrations (MBCs) were determined after 41 days of incubation by BACTEC. 1,4‐Benzoxazin‐2‐ones bearing the unsubstituted benzo moiety showed the most promising activities (MBC = 5.00 µg/ml). For most active compounds, antibacterial activities were determined daily during the 41 days. The most promising compound showed a bacteriostatic effect at a concentration of 0.31 µg/ml on Day 4 of incubation, 0.62 µg/ml on Day 6, 2.50 µg/ml on Day 9, and 5.00 µg/ml on Day 41. All studied compounds, along with some of their reported analogs, were docked to 35 proteins of M. tuberculosis to find their potent targets in these organisms. As a result of reverse docking, aspartate 1‐decarboxylase, panD, was selected as the most appropriate target. Docking of the most active compounds to mutant panD from pyrazinamide‐resistant strains of M. tuberculosis implies that they would not be active against these strains. Considering that most of pyrazinamide clinical resistance cases are due to loss‐of‐function mutations in pyrazinamidase, pncA, compounds from this study could be useful drugs for the treatment of some cases of pyrazinamide‐resistant tuberculosis.

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Spiroheterocyclization of Pyrrolobenzoxazinetriones under the Action of Thiobenzamide. Synthesis of Spiro[thiazolo-5,2′-pyrroles]

Cited by 10 publications

References 11 publications

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

Facile regiodivergent synthesis of spiro pyrrole-substituted pseudothiohydantoins and thiohydantoins via reaction of [e]-fused 1H-pyrrole-2,3-diones with thiourea

Annulation of 1H-pyrrole-2,3-diones by thioacetamide: an approach to 5-azaisatins

Synthesis, in vitro antibacterial activity against Mycobacterium tuberculosis, and reverse docking‐based target fishing of 1,4‐benzoxazin‐2‐one derivatives

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