Synthesis of 2-aminothiazoles containing 3-hydroxypyran-4-one fragment based on condensation of substituted α-arylaminoketones with thiourea

?

Synthesis of 2-aminothiazoles containing 3-hydroxypyran-4-one fragment based on condensation of substituted α-arylaminoketones with thiourea

Journal of Heterocyclic Chemistry. 2024. Vol. 61. No. 10. P. 1531–1541.

Komogortsev A. N., Melekhina V. G., Milyutin C. V., Lichitsky B. V.

Condensation of α-arylaminoketones bearing 3-hydroxypyran-4-one fragment with thiourea was studied. Based on considered investigation, the method for the synthesis of terarylenes with 2-aminothiazole bridge was elaborated. The presented process is the first example of construction of thiazole core starting from α-aminoketone precursor. The advantages of developed approach are easily available starting materials and convenient isolation of target products avoiding chromatographic purification. The structure of one of prepared products was confirmed by x-ray analysis. The synthetic utility of obtained 2-aminothiazoles with allomaltol substituent was demonstrated by reaction at amino and hydroxyl groups.

Language: English

DOI

Text on another site

Keywords: condensation

Tandem, Catalyst-Free C−C Synthesis of Nitriles from Aldehydes and Methyl Cyanoacetate with Sodium Hypophosphite

Korochantsev V., Artemy Fatkulin, Podyacheva E. et al., European Journal of Organic Chemistry 2024 Vol. 28 No. 4 Article e202401108

Saturated carbon chain elongation is a common refrain in numerous synthetic pathways. While the formation of C-C single bonds is of primary importance in organic synthesis, simultaneous introduction of functional groups such as nitrile or ester can reasonably increase its practical utility to prepare multifunctional products. Knoevenagel reaction is one of the powerful tools to ...

Added: January 23, 2025

O-Alkylation Redirected Condensation of 5-Hydroxy-1,2-oxazine-6-ones with Primary Amines for Synthesis of 5-Hydroxyiminopyridine-2,6(1H,3H)-diones

Nizovtsev A., Sokolov A., Smirnov A. et al., ChemistrySelect 2021 Vol. 6 No. 34 P. 8938–8941

Herein we report a short and general protocol for synthesis of potentially biologically active pyridine-2,6-diones. The approach is based on the redirection of the condensation of the intermediates of Dornow reaction – 5-hydroxy-1,2-oxazine-6-ones with primary amines by their prior O-alkylation. Such manipulation blocks their transformation into isoxazoles and allows one to obtain a library of 30+ ...

Added: September 9, 2021

High temperature pure carbon nanoparticle formation: Validation of AIREBO and ReaxFF reactive molecular dynamics

Orekhov N. D., Ostroumova G., Stegailov V., Carbon 2020 Vol. 170 P. 606–620

Molecular dynamics with reactive interatomic potentials is the only computationally feasible approach for modeling at the atomistic level the formation of carbon nanoparticles from gas state. Such models require thousands of atoms and millions of time steps that is beyond the current capabilities of first principles electronic structure calculations. A continuously growing variety of available ...

Added: October 31, 2020

Nitroacetic esters in the regioselective synthesis of isoxazole-3,5-dicarboxylic acids derivatives

Smirnov A., Zaitseva E., Belozerova O. et al., Journal of Organic Chemistry 2019 Vol. 84 No. 23 P. 15417–15428

An efficient and high-yielding strategy to prepare “unsymmetrical” 4-aryl-isoxazol-3,5-dicarboxylic acid derivatives from nitroacetic esters and aromatic aldehydes has been developed. The strategy is based on the isolation and usage of the previously missed intermediate of the Dornow reaction—5-hydroxy-6-oxo-4-aryl-6H-1,2-oxazine-3-carboxylates. In addition, the mechanism of the Dornow reaction was partially revised. ...

Added: September 29, 2020

Route to 1,2,4-and 1,2,5-oxadiazole ring assemblies via a one-pot condensation/oxidation protocol

Ananyev I., Тесленко Ф. Е., Чураков А. et al., Tetrahedron Letters 2020 Vol. 61 No. 13 P. 151678-1–151678-5

A novel one-pot approach for the synthesis of 1,2,4- and 1,2,5-oxadiazole ring assemblies has been developed. The synthetic strategy involves the condensation of furoxanyl amidoximes with aldehydes and subsequent iodine-mediated oxidation of the intermediate 1,2,4-oxadiazolines. The analogous reaction of 4-aminofuroxanyl-3-carboxamidoxime results not only in formation of the 1,2,4-oxadiazole subunit, but also rearrangement of the furoxan ...

Added: August 11, 2020

On dusty plasma formation in Martian ionosphere

Reznichenko Y. S., Dubinskii A. Y., Popel S. I., Journal of Physics: Conference Series 2020 Vol. 1556 P. 012072

A self-consistent model for the formation and evolution of dusty plasmas in the Martian ionosphere is developed. The effects of the initial distributions of dust particles, as well as condensation and absorption of carbon dioxide and water molecules by dust particles, are studied. Theory values of characteristic sizes of dust grains and their charges are obtained. The theoretical values ...

Added: July 7, 2020

Environmentally Safe Techniques In The Recycling Of Mercury-containing Materials

Maslennikova I., Kovalev V., Eronko O. et al., WIT Transactions on Ecology and The Environment 2014 Vol. 190 P. 551–556

Protection of the environment can be achieved by creating conditions that ensure the complete absence, or at least minimal content, of hazardous substances in industrial waste. Therefore, in production processes where the main and/or additive product is material with mercury content, the prevention of mercury vapor emissions into the atmosphere is an essential prerequisite for ...

Added: March 25, 2015