A straightforward metal-free synthesis of 2-substituted thiazolines in air

Trose, Michael; Lazreg, Faïma; Lesieur, Mathieu; Cazin, Catherine S. J.

doi:10.1039/c5gc00286a

Cited by 21 publications

(6 citation statements)

References 35 publications

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“…Condensation of aminothiols with arylnitriles offers a convenient route for the synthesis of 2‐arylthiazolines. However, most of the transformations of nitriles and aminothiols into thiazolines involve the use of strong bases,‐ or catalytic reagents such as cellulose sulfuric acid, phosphotungstic acid under microwave irradiation, Cu complexes, 1,3‐dibromo‐5,5‐dimethylhydantoin, or 1‐butyl‐3‐methylimidazolium tribromide . Even though these innovative synthetic strategies provide new routes for the synthesis of 2‐arylthiazolines, yet they usually suffer from a variety of drawbacks including harsh reaction conditions, use of strong bases, use of expensive and/or less abundant metal catalysts or reagents and limited substrate scope.…”

Section: Introductionmentioning

confidence: 99%

A Base‐ and Metal‐free Protocol for the Synthesis of 2‐Aryl/heteroaryl Thiazolines

2017

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A simple and efficient base‐ and metal‐ free protocol for the synthesis of 2‐aryl/heteroarylthiazoline from aryl/heteroaryl nitriles and cysteamine hydrochloride is reported. This method is applicable to a series of aryl/heteroaryl nitriles containing different substituents such as halides, amines, substituted azoles, etc. and furnishes the corresponding thiazolines in upto 99% yields. A selective synthesis of mono‐ or bis‐thiazoline in more than 90% yield was also observed by modifying the duration of the reaction. This novel methodology has been utilized for the synthesis of some important 2‐aryl/heteroarylthiazoline scaffolds which form a part of many biologically active molecules. A probable reaction mechanism involving the formation of highly activated arylimino chloride is also given.

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Section: Introductionmentioning

confidence: 99%

A Base‐ and Metal‐free Protocol for the Synthesis of 2‐Aryl/heteroaryl Thiazolines

2017

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“…Cazin conditions [ 32 ] provided a low yield for 25 ( Table 2 , experiment 1), observing an incomplete reaction. Lengthening the reaction time (experiment 2) did not improve the outcome, nor did a greater amount of base (experiment 3), which caused the yield to drop sharply due to the hydrolysis of benzonitrile to carboxylic acid.…”

Section: Resultsmentioning

confidence: 99%

N-Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies

Fuentes-Gutiérrez

Curiel-Quesada

Correa‐Basurto

et al. 2020

IJMS

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Quorum sensing is a communication system among bacteria to sense the proper time to express their virulence factors. Quorum sensing inhibition is a therapeutic strategy to block bacterial mechanisms of virulence. The aim of this study was to synthesize and evaluate new bioisosteres of N-acyl homoserine lactones as Quorum sensing inhibitors in Chromobacterium violaceum CV026 by quantifying the specific production of violacein. Five series of compounds with different heterocyclic scaffolds were synthesized in good yields: thiazoles, 16a–c, thiazolines 17a–c, benzimidazoles 18a–c, pyridines 19a–c and imidazolines 32a–c. All 15 compounds showed activity as Quorum sensing inhibitors except 16a. Compounds 16b, 17a–c, 18a, 18c, 19c and 32b exhibited activity at concentrations of 10 µM and 100 µM, highlighting the activity of benzimidazole 18a (IC50 = 36.67 µM) and 32b (IC50 = 85.03 µM). Pyridine 19c displayed the best quorum sensing inhibition activity (IC50 = 9.66 µM). Molecular docking simulations were conducted for all test compounds on the Chromobacterium violaceum CviR protein to gain insight into the process of quorum sensing inhibition. The in-silico data reveal that all 15 the compounds have higher affinity for the protein than the native AHL ligand (1). A strong correlation was found between the theoretical and experimental results.

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“…20 While trying to expand this base-catalyzed protocol to the synthesis of 2-substituted oxazolines, using benzonitrile 1a and ethanolamine 2a as model substrates, we found that a catalytic amount of the base (10 mol%) was solely capable to promote this reaction (Table 1). Strong bases, such as alkali hydroxides (Table 1, entries 2 and 3) and tert-butoxides (Table 1, entry 4), gave only poor conversions, whereas slightly better results were obtained using weak bases, especially Na 2 CO 3 and NaOAc (Table 1, entries 6 and 9, respectively).…”

Section: Resultsmentioning

confidence: 99%

Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols

et al. 2015

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A straightforward metal-free synthesis of 2-substituted thiazolines in air

Abstract: A range of 2-substituted 4,5-dihydrothiazoles was easily synthesised from the reaction of nitriles with cysteamine in the presence of a catalytic amount of NaOH.

Cited by 21 publications

References 35 publications

A Base‐ and Metal‐free Protocol for the Synthesis of 2‐Aryl/heteroaryl Thiazolines

A Base‐ and Metal‐free Protocol for the Synthesis of 2‐Aryl/heteroaryl Thiazolines

N-Heterocycles Scaffolds as Quorum Sensing Inhibitors. Design, Synthesis, Biological and Docking Studies

Copper N-Heterocyclic Carbene Complexes As Active Catalysts for the Synthesis of 2-Substituted Oxazolines from Nitriles and Aminoalcohols

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