Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole

Izmest’ev A.; Karnoukhova V.; A. A. Larin; Kravchenko A.; Leonid L. Fershtat

doi:10.3390/ijms232213820

Publications

?

Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole

International Journal of Molecular Sciences. 2022. Vol. 23. No. 22. Article 13820.

Izmest’ev A., Karnoukhova V., Larin A. A., Kravchenko A., Leonid L. Fershtat

Methods for the synthesis of two types of isomeric dispirocompounds based on imidazothiazolotriazine and pyrrolidineoxindole, differing in the structure of imidazothiazolotriazine fragment, namely, linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine- 4′,3″-indolines] and angular dispiro[imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3′-pyrrolidine-4′,3″-indolines] were proposed. The first method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from paraformaldehyde and N-alkylglycine derivatives to the corresponding oxindolylidene derivatives of imidazothiazolotriazine. The cycloaddition leads to a mixture of two diastereomers resulted from anti- and syn-approaches of azomethine ylide in approximately a 1:1 ratio, which were separated by column chromatography. Another method consists in rearrangement of linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine-4′,3″-indolines] into hitherto unavailable angular dispiro[imidazo[4,5-e]thiazolo[2,3-c]-[1,2,4]triazine-7,3′-pyrrolidine-4′,3″-indolines] upon treatment with KOH. It was found that the anti-diastereomer of linear type underwent rearrangement into the isomeric angular syn-diastereomer, while the rearrangement of the linear syn-diastereomer gave the angular anti-diastereomer.

Research target: Chemistry

Language: English

DOI

Text on another site

Keywords: rearrangement

When universal machine learning models fail in capacitance prediction for carbon-based supercapacitors: Leakage-aware validation and electrolyte screening

Makarov D. M., Kalikin N., Fashchevsky K. A. et al., Electrochimica Acta 2026 Vol. 579 Article 150159

Machine learning (ML) has become a powerful tool for accelerating the development of carbon-based supercapacitors; however, most published models assume that a single predictive framework can describe both conventional porous carbons and hybrid carbon electrodes. Here, we test this assumption using a comprehensive benchmark dataset and an extended literature-curated dataset enriched with synthesis- and electrolyte-related descriptors. Three ML algorithms ...

Added: October 13, 2026

Electrochemical reduction of cyanide on conjugated copper-organic framework Cu3(HHTP)2 monolayer: A dispersion-corrected DFT investigation.

Shi R., Yu Y., Chibisov A., International Journal of Hydrogen Energy 2025 Vol. 107 P. 52–62

Cyanide containing wastewater can cause livestock death and reduce agricultural production and electrochemical reduction of cyanide (CNRR) is a promising way to eliminate its harm and turn waste into valuable products. However, the reaction mechanism and function of electrocatalysts for CNRR have not been fully understood yet. Herein we identify a two-dimensional (2D) conductive copper-organic ...

Added: October 11, 2026

Advances in colloidal anisotropic nanocrystals for high-efficiency light-emitting diodes

Zhukov A., Chen F., Zeng Y. et al., Nanoscale 2026 Vol. 18 No. 36 P. 19223–19253

Colloidal semiconductor nanocrystals have emerged as promising materials for next-generation light-emitting diodes (LEDs) owing to their solution processability, tunable emission wavelengths, narrow emission linewidths, and high photoluminescence quantum yields. Among them, anisotropic nanocrystals, including one-dimensional nanorods (NRs) and two-dimensional nanoplatelets (NPLs), offer additional opportunities for controlling transition dipole moment orientation and light out-coupling efficiency. These ...

Added: October 2, 2026

Effect of the hydrogen bond donor nature on the extraction ability of a tributyl phosphate-based deep eutectic solvent

Мальцева В. Е., Ananyev I., Milevskii N. et al., Molecular Systems Design and Engineering 2026 Vol. 11 No. 7 P. 691–704

The use of hydrophobic deep eutectic solvents (DESs) as extractants for metal ion separation is largely due to the ease of their preparation and the possibility of modifying them depending on the composition of the metal mixture to be separated. However, the most common approach to DES modification involves the replacement of the extractant, while ...

Added: October 2, 2026

Crystal Structure and 35Cl NQR Spectroscopy in Сhlorinated closo-Dodecaborate Clusters {[(Me2CO)Ag(μ-Me2CO)2Ag(Me2CO)][μ-B12Cl12]}n and {[DMFAg(μ-DMF)2AgDMF][μ-B12Cl12]}n

Мальцева В. Е., Ananyev I., Golubev A. V. et al., Russian Journal of Inorganic Chemistry 2026 Vol. 71 P. 724–736

Two voluminous polymer silver(I) salts of perchlorinated dodecoborate clusters, {[(Me2CO)Ag(μ-Me2CO)2Ag(Me2CO)][μ-B12Cl12]}n (1) and {[DMFAg(μ-DMF)2AgDMF][μ-B12Cl12]}n (2) were synthesized. The 35Cl nuclear quadrupole resonance (NQR) spectroscopy supplemented with the X-ray diffraction data was applied for identifying and analyzing noncovalent interactions Cl···X in these salts. Whereas in X-ray diffraction, noncovalent interactions are associated with the presence of the shortened ...

Added: October 2, 2026

High-Resolution X‑ray Diffraction of TeII-Centered Chalcogen Bonds: Direct Visualization of σ–Holes and Quantitative Bonding Analysis

Мальцева В. Е., Rozhkov A., Ananyev I. et al., Inorganic Chemistry 2026 Vol. 65 No. 22 P. 12484–12496

Despite the well-established importance of chalcogen bonding in crystal engineering and supramolecular chemistry, experimental charge density data for TeII-centered chalcogen bonds have remained entirely absent, leaving the electronic nature of these interactions uncharacterized at the level of directly measured electron density. Here, we report the first high-resolution X-ray diffraction (HRXRD) study of TeII-centered chalcogen bonds, ...

Added: October 2, 2026

High Temperature Oxidation Resistance of Off-Stoichiometric (Ni39.6Co29.3Cr10Al15.8Ta3.3Nb2)98.5B1.5 Chemically Complex Intermetallic Alloy

Ostovari Moghaddam A., Mehrabi-Kalajahi S., Solizoda I. A. et al., Metals and Materials International 2026 P. 1–9

Off-stoichiometric boron-doped chemically complex intermetallic alloys (CCIMAs) have recently emerged as a new avenue for overcoming the low temperature brittleness of ordered superlattices. However, their behavior at high temperatures remains unexplored. In this study, a novel (Ni39.6Co29.3Cr10Al15.8Ta3.3Nb2)98.5B1.5 CCIMA was prepared and its oxidation resistance over a wide temperature range (500 °C–950 °C) was studied. The ...

Added: October 1, 2026

MPI+OpenMP implementation of resolution-of-the-identity Hartree-Fock method exploiting permutational symmetry of three-center electron repulsion integrals

Kashpurovich I., Oleynichenko A., Stegailov V., Supercomputing Frontiers and Innovations 2026 Vol. 13 No. 1 P. 52–73

We report a high-performance implementation of the resolution-of-the-identity Hartree–Fock method that fully exploits the permutational symmetry of three-center electron repulsion integrals (ERI). The present implementation adopts a hybrid MPI+OpenMP parallelization strategy. Two different algorithmic approaches (with and without the pre-transformation of ERIs) are compared. A custom data layout introduced previously is employed. Designed to efficiently ...

Added: September 28, 2026

Thermodynamic Stabilization of PbS Quantum Dots for High-Performance Short-Wave Infrared Photodetection

Li Y., Han J., Zaman N. et al., ACS Applied Materials & Interfaces 2026 Vol. 18 No. 39 P. 54241–54251

The development of lead sulfide (PbS) quantum dot (QD) photodetectors for short-wave infrared (SWIR) applications has been fundamentally limited by the thermodynamic instability of large PbS QD facets, which leads to aggregation and epitaxial fusion. In this work, robust thermodynamic stabilization was achieved by introducing methylammonium chloride (MACl) in PbS QD surface passivation, as validated ...

Added: September 26, 2026

Merging Johnson–Claisen and Aromatic Claisen [3,3]-Sigmatropic Rearrangements: Ytterbium Triflate/2,6-Di-tert-butylpyridine Catalytic System

Ikonnikova V., Zhigileva E., Al Mufti A. et al., Journal of Organic Chemistry 2023 Vol. 88 No. 14 P. 9737–9749

Added: August 18, 2023

Divergent Synthesis of Five-Membered Nitrogen Heterocycles via Cascade Reactions of 4-Arylfuroxans

Chaplygin D., Ananyev I., Fershtat L. et al., Synthesis 2020 Vol. 52 No. 18 P. 2667–2678

A novel method for the synthesis of a diverse series of functionally substituted five-membered heterocyclic compounds via atom-economic, regio-, and diastereoselective one-pot reaction cascade was developed. This approach involves a ring opening in 4-arylfuroxans to alpha-oximinoarylacetonitrile oxides followed by [3+2] cycloaddition to various dipolarophiles to afford multisubstituted isoxazoles and isoxazolines. Subsequent azole-azole rearrangement of (oximino)isoxazolines/-isoxazoles, ...

Added: April 12, 2021

Sigmatropic Rearrangement-Based Synthesis of 4-Alkenyl-1,3-dithiol-2-ones

Ostrovskis P., Mikhaylov Andrey A., Zard S., Organic Letters 2019 Vol. 21 No. 10 P. 3726–3729

A series of conjugated 4-alkenyl-1,3-dithiol-2-ones have been prepared by microwave-assisted rearrangement of S-(4-acyloxy-2-alkynyl)-O-ethyl xanthates in moderate to good yields. The synthetic approach is based on a combination of [3,3] and [1,5] sigmatropic rearrangements as well as the intermediacy of a reactive betaine that induces the ionic elimination of the acyloxy group. The [1,5] sigmatropic rearrangement was ...

Added: September 29, 2020

Tandem Condensation/Rearrangement Reaction of 2-Aminohetarene N-Oxides for the Synthesis of Hetaryl Carbamates

Ananyev I., Быстров Д., Жилин Е. et al., Advanced Synthesis and Catalysis 2018 Vol. 360 No. 16 P. 3157–3163

A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2-aminohetarene N-oxides was developed. The developed reaction is suitable for both five- and six-membered heterocycles and proceeds through the condensation of 2-aminohetarene N-oxide with trimethyl orthoformate followed by intramolecular N-oxide oxygen transfer. For five-membered hetarene N-oxides (furoxans), the intramolecular rearrangement is catalyzed by ...

Added: October 4, 2019

Примеры расходящихся рядов Фурье для широкого класса переставленных систем Уолша-Пэли

Polyakov I. V., Вестник Московского университета. Серия 1: Математика. Механика 2012 Т. 1 № 6 С. 3–8

In this paper the rearranged Walsh system is considered. We prove that exists integrable function L o( sqrt ln+ L ) for which Fourier series with respect to the rearranged Walsh system diverges almost everywhere. ...

Added: April 2, 2013