Cascade Reaction of Tertiary Enaminones, KSCN, and Anilines: Temperature-Controlled Synthesis of 2-Aminothiazoles and 2-Iminothiazoline

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(14), P. 9171 - 9183

Published: July 5, 2022

A one-pot cascade strategy for the synthesis of 2-aminothiazole derivatives by tertiary enaminones, KSCN, and anilines was developed. By changing reaction temperature, three-component could be transformed in different ways to obtain moderate good yields polysubstituted 2-aminothiazoles 2-iminothiazolines. This protocol provides an efficient concise approach accessing with potential bioactivity from readily accessible building blocks reagents.

Language: Английский

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The synthesis of O/S-heterocycles starting from β-nitrostyrenes: A recent update

Tetrahedron, Journal Year: 2023, Volume and Issue: 149, P. 133717 - 133717

Published: Nov. 2, 2023

Language: Английский

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Bromonitroalkenes as efficient intermediates in organic synthesis

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(24), P. 4801 - 4838

Published: Jan. 1, 2024

Bromonitroalkenes are useful molecules in synthetic organic chemistry. They mainly prepared from nitroalkenes

Language: Английский

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An In‐Depth Review on Recent Progress in Synthetic Approaches and Biological Activities of Thiazol‐2(3H)‐Imine Derivatives

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(32)

Published: Aug. 22, 2024

Abstract This review presents the in‐dept analysis of synthetic approaches towards thiazol‐2( 3H )‐imine and embarks at its various biological properties published during 2000 to 2023. The most important method synthesis involves reaction substituted thioureas α‐halo carbonyl compounds, condensation nucleophilic addition 2‐amino‐1,3‐thiazoline with aldehydes. Additionally, isothiocyanate‐based multicomponent synthesis, α‐nitroepoxides have been proved as benign precursors for this motif. Several eco‐friendly solvent‐free from diazonium salts, acetylenes, tertiary enaminones thiosemicarbazides also reported. epitome is a unique combination methods well activities like anti‐inflammatory, anti‐bacterial, anti‐cancer, anti‐leishmanial, anti‐microbial, herbicidal, anti‐HIV, may be valuable tool researchers tailor procedures according specific target structures applications. Moreover, enlightens applications platelet GPIIB/IIIA receptor antagonists, alkaline phosphatase inhibitors, neurodegenerative drug Pifithrin‐α analogues, skin whitening agents.

Language: Английский

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Developments and applications of α-bromonitrostyrenes in organic syntheses

RSC Advances, Journal Year: 2024, Volume and Issue: 14(21), P. 14835 - 14846

Published: Jan. 1, 2024

In this work, we have described the use of α-bromonitrostyrenes in synthesis a wide variety carbocyclic and heterocyclic compounds under organocatalysis, metal catalysis, base-catalysis systems as well catalyst-free reactions.

Language: Английский

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1-Aryl-3-nitro- and 3-Bromo-3-nitroprop-2-en-1-ones: Synthesis and Structural Features

Russian Journal of General Chemistry, Journal Year: 2024, Volume and Issue: 94(3), P. 497 - 507

Published: March 1, 2024

Abstract A method for producing a number of ( E )-1-aryl-3-nitroprop-2-en-1-ones based on synthetic condensation–dehydration strategy has been optimized. New Z )-1-aryl-3-bromo-3-nitroprop-2-en-1-ones have synthesised from using halogenation-dehydrohalogenation to )-1-aryl-3-nitroprop-2-en-1-ones. The fine structure nitro- and bromonitroenketones it’s features were determined by 1 H– H NOESY NMR X-ray diffraction analysis.

Language: Английский

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Efficient synthesis of functionalized 2-iminothiazolines by ultrasonication under solvent-free conditions and access to 5-aryl-2-iminothiazolines

Results in Chemistry, Journal Year: 2022, Volume and Issue: 4, P. 100301 - 100301

Published: Jan. 1, 2022

An ultrasound assisted methodology has been developed for rapid synthesis of a series biologically important 2-iminothiazolines from easily available α-bromoketones and thioureas under solvent- catalyst-free conditions at room temperature in open air. The are found to exhibit moderate activity against both the representative Gram positive negative bacteria, suggesting possible scope using them as antimicrobials. Additionally Suzuki cross-coupling 5-bromo-2-iminothiazolines with organoboronic acids produced fully substituted 5-aryl-2-iminothiazolines good yield.

Language: Английский

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Reaction of alkyl 3-bromo-3-nitroacrylates with substituted hydrazines. Synthesis of N′-substituted alkyl 3-nitropyruvate hydrazones

Russian Chemical Bulletin, Journal Year: 2022, Volume and Issue: 71(4), P. 740 - 749

Published: April 1, 2022

Language: Английский

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Iodine promoted cyclization of N,N′-diphenylthiocarbamides with enaminones: a protocol for the synthesis of poly-substituted 2-iminothiazolines

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(43), P. 8533 - 8537

Published: Jan. 1, 2022

An iodine promoted cyclization reaction between N , ′-diphenylthiocarbamides and enaminones was achieved, providing a series of poly-substituted 2-iminothiazolines.

Language: Английский

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Preparation of 4-Arylthiazol-2(3H)-ones and the Three-Component Synthesis of Multidentate 5,5′-Methylenebis[4-arylthiazol-2(3H)-one] Ligands

Synthesis, Journal Year: 2022, Volume and Issue: 55(01), P. 141 - 149

Published: Aug. 25, 2022

Abstract The synthesis of 4-arylthiazol-2(3H)-ones is reported employing a novel and mild methodology using benign solvents. In second objective, the multicomponent preparation 5,5′-methylenebis[4-arylthiazol-2(3H)-ones] described following same strategy. analysis mechanism also studied confirmed chemical tests.

Language: Английский

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