Synthesis Of Thiazolo Research Articles

Lewis Acid‐Mediated Synthesis of Thiazolo[3,2‐a] Hydrazone‐Based Organic Semiconducting Microwires

Organic semiconducting wires have captured broad attention in recent years due to its tremendous applications in various fields. The structural and chemical versatility, easy fabrication, tunable properties, and low cost have made their inevitable presence in electronics and optoelectronics. Herein, the synthesis and characteristic description of a new thiazolo[3,2‐a] hydrazone‐based organic semiconducting microwire synthesized by the Lewis acid‐based condensation reaction between methyl (Z)‐2‐(2‐(2‐methoxy‐2‐oxoethylidene)‐3‐oxo‐2,3‐dihydrothiazolo[3,2‐a]indol‐9‐yl)‐2‐oxoacetate and phenyl hydrazine under reflux conditions is reported. The optical, electrical, and semiconducting nature of the material is revealed from the specular reflectance study. When the Tauc plot analysis reveals a direct bandgap of 2.03 eV, the hot probe test suggests the nature of the majority of charge carriers as electrons, indicating the hydrazone as an organic semiconductor. The long wire‐like morphology with a high aspect ratio makes the molecule conceivable for advanced optoelectronic applications.

Recent advances in the synthesis of thiazolo[4,5-b]pyridines. Part 2: Focus on thiazole annulation to pyridine ring (microreview)

Recent advances in the synthesis of thiazolo[4,5-b]pyridines. Part 2: Focus on thiazole annulation to pyridine ring (microreview)

Recent advances in the synthesis of thiazolo[4,5-b]pyridines. Part 1: Focus on pyridine annulation to thiazole ring (microreview)

Recent advances in the synthesis of thiazolo[4,5-b]pyridines. Part 1: Focus on pyridine annulation to thiazole ring (microreview)

Sabinene: A New Green Solvent Used in the Synthesis of Thiazolo[5,4-b]pyridines by Thermal or Microwave Activation.

Following the work already carried out in our laboratory on eucalyptol, a new green solvent derived from biomass, we are now looking at sabinene as another new green solvent. Sabinene is also derived from biomass, has no known toxicity and can be recycled by distillation. We have shown that it can be used as it is or distilled to synthesize thiazolo[5,4-b]pyridine heterocycles by thermal activation or microwave irradiation. This new solvent was compared with various conventional and green solvents. The conditions were optimised to enable us to carry out the syntheses in satisfactory yields, and we were able to show that sabinene, a natural bicyclic monoterpene, could be used effectively as a solvent.

Synthesis, biological evaluation, and molecular docking studies of thiazolo[4,5‐b]pyridin‐5‐ones as antimicrobial agents

AbstractHerein we report the design and synthesis of thiazolo[4,5‐b]pyridin‐5‐ones and evaluation of their antimicrobial activity. The design was based on a molecular hybridization approach. Evaluation of their antibacterial activity revealed that these compounds generally showed moderate antibacterial activity. The best activity was achieved for compound 4p with MIC/MBC in the range of 0.12–0.47 and 0.23–0.94 mg mL−1 respectively. Three compounds (4g, 4n, and 4p) were tested against three resistant strains, namely MRSA, p.aeruginosa, and E.coli, showing higher inhibition potential than the reference drug ampicillin. These three compounds also were tested for their ability to inhibit biofilm formation, with two of them showing better activity than streptomycin in a concentration of MIC (4p) and ampicillin in both concentrations (MIC and 0.5 MIC). As far as antifungal activity is concerned, the best activity was observed for compound 4i with MIC at 0.12–0.47 mg mL−1 and MFC at 0.23–0.94 mg m−1. According to docking studies, the predicted inhibition of E.coli MurB enzyme is probably a putative mechanism of the antibacterial activity of these compounds, while inhibition of 14a‐lanosterol demethylase is probably the mechanism of their antifungal activity.

BF3·Et2O catalyzed transannulation of pyridotriazoles with isothiocyanates: synthesis of thiazolo[3,4-a]pyridin-3-imines

The synthesis of thiazolo[3,4-a]pyridin-3-imines, through denitrogenative transannulation of pyridotriazoles, under transition metal-free conditions is described.

The first Q-Tube based high-pressure synthesis of anti-cancer active thiazolo[4,5-c]pyridazines via the [4\u2009+\u20092] cyclocondensation of 3-oxo-2-arylhydrazonopropanals with 4-thiazolidinones

A novel and efficient protocol for the synthesis of thiazolo[4,5-c]pyridazine derivatives was developed. The approach utilizes a high pressure Q-Tube reactor to promote cyclocondensation reactions between 3-oxo-2-arylhydrazonopropanals and 4-thiazolidinones. The process has a significantly high atom economy and a broad substrate scope, as well as being applicable to gram scale syntheses. The in vitro cytotoxic activities of the synthesized thiazolo[4,5-c]pyridazine derivatives were examined utilizing a MTT colorimetric assay with doxorubicin as a reference anti-cancer drug and three human cancer cell lines including HCT-116 (colon), MCF-7 (breast) and A549 (lung). The results show that thiazolopyridazines 7c, h, k and p have high cytotoxic activity against the MCF-7 cell line with respective IC50 values of 14.34, 10.39, 15.43 and 13.60 μM. Moreover, the thiazolopyridazine derivative 7s also show promising cytotoxic activity against the HCT-116 cell line with IC50 = 6.90 μM . Observations made in this effort serve as a basis for further investigations into the design and preparation of new anti-cancer drugs.

SYNTHETIC METHODOLOGIES TOWARD THIAZOLOTHIAZOLES

The data on the methodologies adopted for the synthesis of thiazolo[4,5- d ]thiazoles and thiazolo[5,4- d ]thiazoles are reviewed. The most relevant publications from the last 10 years are discussed.

Synthesis of Thiazolo[3,2‐b] [1,2,4]triazoles through Pd‐Catalyzed Copper‐Free Sonogashira Coupling Reaction

AbstractThe synthesis of 2‐substituted thiazolo[3,2‐b] [1,2,4]triazoles is accomplished copper‐free, Pd‐catalyzed Sonogashira reaction of 6‐(iodomethyl)‐2‐methylthiazolo[3,2‐b][1,2,4]triazole with terminal alkynes in DMF at 70 °C. The coupling reaction of phenylacetylene and 4‐ethynyltoluene gave the desired products in high yields. While, the Sonogashira reaction of alkynes such as 1‐hexyne, 1‐octyne, propargyl alcohols, and propargyl amines afforded the products in good yields.

Synthesis of thiazolo[2,3-b]quinazoline derivatives via base-promoted cascade bicyclization of o-alkenylphenyl isothiocyanates with propargylamines.

A highly efficient cascade bicyclization reaction of o-alkenylphenyl isothiocyanates with propargylamines has been developed, which affords a series of thiazolo[2,3-b]quinazolines in good to excellent yields by using K2CO3 as a base in MeCN at 80 °C. This method is transition-metal-free and operationally simple with broad functional group tolerance. Mechanistically, 6-exo-trig hydroamination followed by 5-exo-dig hydrothiolation was involved in this transformation.

Recent progress in the synthesis of thiazolo[3,2-a]pyrimidine compounds

In this paper, the progress in the synthesis of thiazole[3,2-a]pyrimidine compounds in the field of medicine and pesticide were reviewed. The main synthetic routes include: (i) synthesis of thiazolo[3,2-a]pyrimidines, spiro thiazolo[3,2-a]pyrimidines and pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines by multicomponent reactions (MCRs). (ii) synthesis of thiazolo[3,2-a]pyrimidines by condensation of pyrimidine-2-thiones, which were obtained by Biginelli reaction between aromatic aldehydes and thiourea, with substituted 2-bromo-1-phenylethanone or chloroacetic acid. (iii) synthesis of pyridothieno-fused thiazolo[3,2-a]pyrimidinones via Pictet–Spengler reaction. (iv) synthesis of pyrido[4,3-d]thiazolo[3,2-a]pyrimidine by reacting 2-aminothiazole with the α, β-unsaturated ketones.

Recent progress in the synthesis of thiazolo[3,2-b][1,2,4]triazoles (microreview)

A summary of the most recent approaches toward synthesis of thiazolo[3,2-b][1,2,4]triazole system is reported. The microreview covers the latest selected examples on the synthesis of thiazolo[3,2-b][1, 2, 4]triazoles via condensation, annulation of a multiple bond or thiirane ring, as well as C–H functionalization of thiazole moiety.

One-pot synthesis of thiazolo[3,4-a]quinoxalines by using 1,2-diamines, aryl isothiocyanates, and ethyl bromopyruvate

One-pot synthesis of thiazolo[3,4-a]quinoxalines by using 1,2-diamines, aryl isothiocyanates, and ethyl bromopyruvate

ChemInform Abstract: Synthesis of Thiazolo[5,4‐d][1,2,4]triazolo[4,3‐a]pyrimidines as a New Class of Heterocyclic Compounds.

AbstractAn efficient synthetic pathway for the formation of derivatives of the novel title heterocyclic system (IX), potential templates in drug discovery, is given.

Efficient One-Pot Three-Component Synthesis of Novel Spiro(Indoline-3,7′-Thiazolo[3,2-a]Pyrimidine) Derivatives

A practical, simple and efficient method for the synthesis of thiazolo[3,2- a]pyrimidine-fused spirooxindoles by a three-component reaction of isatins, malononitrile and 2-amino-2-thiazoline in the presence of Cul as catalyst in ethylene glycol is reported.

Synthesis of Thiazolo[5,4-d][1,2,4]Triazolo[4,3-a]Pyrimidines as a New Class of Heterocyclic Compounds

A new series of 2-aminothia zolo[5,4- d]pyrimidines has been synthesised by treating various amines with the new intermediate, 2,5-dichloro-7-methylthiazolo[5,4- d]pyrimidine. Sequential treatment of the amino derivatives with hydrazine hydrate and triethyl orthoesters gave thiazolo[5,4- d][1,2,4]triazolo[4,3- a]pyrimidines as derivatives of a novel heterocyclic system.

Synthesis of Thiazolo[5,4-f]quinazolin-9(8H)-ones as Multi-Target Directed Ligands of Ser/Thr Kinases.

A library of thirty novel thiazolo[5,4-f]quinazolin-9(8H)-one derivatives belonging to four series designated as 12, 13, 14 and 15 was efficiently prepared, helped by microwave-assisted technology when required. The efficient multistep synthesis of methyl 6-amino-2-cyano- benzo[d]thiazole-7-carboxylate (1) has been reinvestigated and performed on a multigram scale. The inhibitory potency of the final products against five kinases involved in Alzheimer’s disease was evaluated. This study demonstrates that some molecules of the 12 and 13 series described in this paper are particularly promising for the development of new multi-target inhibitors of kinases.

Synthesis of new sulfonamide derivatives of thiazolo[3,2-a]quinazolin-5-one

A general procedure has been proposed for the synthesis of thiazolo[3,2-a]quinazolin-5-one derivatives containing a sulfonamide group on C7 via intramolecular nucleophilic substitution of halogen in 2-halo-5-sulfamoyl-N-(1,3-thiazol-2-yl)benzamides. The effects of the degree of activation of the initial compound and halogen nature on the yield of the target products have been analyzed.

Synthesis and characterization of highly stable superparamagnetic CoFe2O4 nanoparticles as a catalyst for novel synthesis of thiazolo[4,5-b]quinolin-9-one derivatives in aqueous medium

A highly stable CoFe2O4 magnetic nanoparticles (MNPs) has been successfully prepared using a combined sonochemical and co-precipitation technique in aqueous medium without any surfactant or organic capping agent. The prepared (MNPs) were characterized with XRD, SEM, EDX, TEM, FT-IR and VSM. These nanoparticles form stable dispersions in aqueous or alcoholic medium. MNPs has been an efficient and environmentally benign nanocatalyst for the one-pot multicomponent synthesis of tetrahydrobenzo[h][1,3] thiazolo[4,5-b]quinolin-9-one 4a-p. The synthesized compounds easy work-up and purification of products by non-chromatographic methods. Highly yield of the corresponding products were obtained within a very short time in presence of just 6mol% of the catalyst.

Design and synthesis of thiazolo[5,4-f]quinazolines as DYRK1A inhibitors, part I.

The convenient synthesis of a library of novel 6,6,5-tricyclic thiazolo[5,4-f] quinazolines (forty molecules) was achieved mainly under microwave irradiation. Dimroth rearrangement and 4,5-dichloro-1,2,3,-dithiazolium chloride (Appel salt) chemistry were associated for the synthesis of a novel 6-aminobenzo[d]thiazole-2,7-dicarbonitrile (16) a versatile molecular platform for the synthesis of various bioactive derivatives. Kinase inhibition of the final compounds was evaluated on a panel of four Ser/Thr kinases (DYRK1A, CDK5, CK1 and GSK3) chosen for their strong implications in various regulation processes, especially Alzheimer’s disease (AD). In view of the results of this preliminary screening, thiazolo[5,4-f]quinazoline scaffolds constitutes a promising source of inspiration for the synthesis of novel bioactive molecules. Among the compounds of this novel chemolibrary, 7i, 8i and 9i inhibited DYRK1A with IC50 values ranging in the double-digit nanomolar range (40, 47 and 50 nM, respectively).