Synthesis of Propyne(ene)oxy-Substituted Spirotetrahydrofurans

Talybov, G. М.; Mamedbeyli, E. G.; Yusubov, F. V.

doi:10.1134/s1070363218120344

Cited by 3 publications

(1 citation statement)

References 12 publications

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“…The reaction comprises the HTIB mediated oxidative cyclization of homoallyl alcohols 105 to substituted spirotetrahydrofuran derivatives 107 using iodine as a catalyst with allyl and propargyl alcohols 106 in high yields (54–72 %) (Scheme 37). [87] …”

Section: Synthesis Of Heterocyclic Compounds Via Oxidative Cyclizationmentioning

confidence: 99%

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

et al. 2022

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Organo hypervalent iodine reagents are nowadays more attractive and versatile reagents for various chemical transformations in synthetic organic chemistry. These reagents are milder and having similar reactivity compared with toxic heavy metal reagents. Organo hypervalent iodine (λ3) reagents are successfully utilized to prepare synthetically and biologically important heterocycles. Hydroxy(tosyloxy)iodobenzene (HTIB) also acknowledged as Koser's reagent uses as an environmentally sustainable alternative to toxic heavy metals for the numerous and valuable organic transformations. The goal of this review is to highlight the recent advancements of the HTIB especially in the construction of heterocycles with various substitution patterns in a well‐organized form via tosyloxylation of ketones and oxidative cyclization methodology. This review compiles the up‐to‐date synthetic advancements of HTIB in the field of heterocycles.

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Section: Synthesis Of Heterocyclic Compounds Via Oxidative Cyclizationmentioning

confidence: 99%

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

et al. 2022

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New Synthetic Approaches to Benzo-Fused Spiro Heterocycles

Musabirov

Гатауллин²

2022

Russ J Org Chem

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Biological Properties of Oleanolic Acid Derivatives Bearing Functionalized Side Chains at C-3

Fontana,

Badalamenti,

Bruno

et al. 2024

IJMS

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Triterpene acids are a class of pentacyclic natural carboxylic compounds endowed with a variety of biological activities including antitumor, antimicrobial, and hepatoprotective effects. In this work, several oleanolic acid derivatives were synthesized by structurally modifying them on the C-3 position. All synthesized derivatives were evaluated for possible antibacterial and antiviral activity, and among all the epimers, 6 and 7 demonstrated the best biological activities. Zone-of-inhibition analyses were conducted against two strains, E. coli as a Gram-negative and S. aureus as a Gram-positive model. Subsequently, experiments were performed using the microdilution method to determine the minimum inhibitory concentration (MIC). The results showed that only the derivative with reduced hydrogen bonding ability on ring A possesses remarkable activity toward E. coli. The conversion from acid to methyl ester implies a loss of activity, probably due to a reduced affinity with the bacterial membrane. Before the antiviral activity, the cytotoxicity of triterpenes was evaluated through a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Samples 6 and 7 showed less than 50% cytotoxicity at 0.625 and 1 mg/mL, respectively. The antiviral activity against SARS-CoV-2 and PV-1 did not indicate that triterpene acids had any inhibitory capacity in the sub-toxic concentration range.

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Synthesis of Propyne(ene)oxy-Substituted Spirotetrahydrofurans

Cited by 3 publications

References 12 publications

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

Hydroxy(tosyloxy)iodobenzene (HTIB): A Convenient Oxidizing Agent for the Synthesis of Heterocycles

New Synthetic Approaches to Benzo-Fused Spiro Heterocycles

Biological Properties of Oleanolic Acid Derivatives Bearing Functionalized Side Chains at C-3

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