CHEMICAL TRANSFORMATIONS OF HETEROCUMULENES GENERATED BY THERMOLYTIC DECARBONYLATION OF 1H-PYRROLE-2,3-DIONES

This work was supported by the Russian Science Foundation, project # 19-13-00290

SYNTHESIS OF ENAMINONES BEARING 1, 4-BENZOTHIAZINE-2-ONE CORE

Enaminones bearing a 1, 4-benzoxazine-2-one A or quinoxaline-2(1H)-one B core are an intensively investigated class of heterocyclic compounds. Interest in them is due to the simplicity of their synthesis and purification, the availability of starting materials and the possibility of their synthesis under mild green conditions. Because of their availability in gram-scale quantities, these compounds were thoroughly investigated for the possibility of practical use. They also proved themselves to be versatile and available building blocks for the synthesis of various heterocyclic systems. That’s why investigations on properties of their 1-thia analogs, 1, 4-benzothiazin-2-ones C, is promising.This work was supported by the Ministry of Science and Higher Education of the Russian Federation (FSNF-2020-0008), Russian Foundation for Basic Research (project no. 17-43-590035) and the Government of Perm Krai

1,3-Dipolar cycloaddition reaction of fused 1H-pyrrole-2,3-diones with nitrones: a divergent approach to pyrroloisoxazoles

This work was supported by the Russian Science Foundation, project № 19-13-00290

Dipyrazolodioxadiazocines as Easily Storable and “Ready to Use” Precursors for in Situ Generation of Enolate-Iminium 1,4-Dipoles: an Atom-Economical Approach Topyrazolo[5,1-d][1,3,5]Dioxazines

The work was supported by Russian Science Foundation, project № 19-13-00290

DIVERGENT REACTIONS OF ESTERS OF ACYLPYRUVIC ACIDS WITH o-PHENYLENEDIAMINE

This work was supported by the Ministry of Science and Higher Education of the Russian Federation (FSNF-2020-0008), Russian Foundation for Basic Research (project no. 20-43-596008) and the Government of Perm Krai. Antimicrobial screening was performed by CO-ADD (The Community for Antimicrobial Drug Discovery), funded by the Wellcome Trust (UK) and The University of Queensland (Australia)

Facile approach to alkaloid-like polycyclic spiroheterocycles via thermal cycloaddition of pyrrolobenzothiazinetriones with olefins

This work was supported by the Ministry of Science and Higher Education of the Russian Federation (FSNF-2020-0008), Russian Foundation for Basic Research (project № 17-43-590035)

CYCLOADDITION OF 1,4-CNCO DIPOLES GENERATED FROM DIPYRAZOLODIOXADIAZOCINES

This work was supported by the Russian Science Foundation, project # 19-13-00290

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

This work is licensed under a Creative Commons Attribution 4.0 International License.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

Regiodivergent dipolar cycloaddition based on pyrrole-2,3-diones

It was previously demonstrated, that thermal decarbonylation of N-substituted 2,3-dihydro-2,3-pyrroldiones afforded imidoylketenes, whose chemical behavior largely depends on the nature of substituents at N-1. It was discovered that N-(diphenylenamino)pyrrolediones experienced facile CO-extrusion at elevated temperatures and the resulting a zwitterionic dihydropyrazolone species, which can be represented by enolate-iminium 1,4-dipole resonance form. In the absence of dipolarophiles, the products of [4+4]-cyclodimerization – bis(pyrazolo)dioxadiazocines – were formed in high yields. To this end, we generated the ketenes in the presence of alkyl vinyl ethers, aldehydes, ketenes, nitriles and isocyanides targeting products of dipolar cycloadditions. We further elaborated on the development of various synthetic schemes involving cycloaddition of these unusual 1,4-dipoles. Dipyrazolodioxadiazocines are shelf-stable "ready-to-use" precursors for an in situ generation of enolate-iminium 1,4-dipoles.This work was supported by the Russian Science Foundation, project № 19-13-00290

REACTION OF 3-ARYL-1-(BENZOTHIAZOL-2-YL)PROPANE-1,3-DIONES WITH ARYLAMINES

This work was supported by the Ministry of Science and Higher Education of the Russian Federation (project no. FSNF-2020-0008), Russian Foundation for Basic Research (project no. 20-43-596008) and the Government of Perm Krai, Scholarship of the President of the Russian Federation for young scientists and graduate students (project no. SP-838.2022.4)