A one-pot synthesis of functionalized ethyl 1,3-thiazole-5-carboxylates from thioamides or thioureas and 2-chloro-1,3-dicarbonyl compounds in an ionic liquid

Yavari, Issa; Sayyed-Alangi, S. Zahra; Hajinasiri, Rahimeh; Sajjadi-Ghotbabadi, Hadi

doi:10.1007/s00706-008-0065-7

Cited by 18 publications

(13 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thiazole ring is an important motif in active biological compounds such as B 1 vitamin (Bakavoli, Beyzaie, Rahimizadeh, Eshghi, & Takjoo 2009, Yavari, Sayyed-Alangi, Hajinasiri, & Sajjadi-Ghotbabadi, 2009Afradi, Foroughifar, Pasdar, & Moghanian, 2016). This heterocyclic system and its derivatives show various properties as drugs for the treatment of cancer , blood cholesterol, blood pressure, and HIV virus infection (Ghasemi et al, 2016;Yavari et al, 2009), they're also featured strongly antibacterial, antifungal and anti-inflammatory activities (Mishra, Tomer, Priyanka, Sharma, Jha, 2012;.…”

mentioning

confidence: 99%

“…This heterocyclic system and its derivatives show various properties as drugs for the treatment of cancer , blood cholesterol, blood pressure, and HIV virus infection (Ghasemi et al, 2016;Yavari et al, 2009), they're also featured strongly antibacterial, antifungal and anti-inflammatory activities (Mishra, Tomer, Priyanka, Sharma, Jha, 2012;.…”

mentioning

confidence: 99%

“…These methodologies include Cook_Heilborn, Tchernic and Hatzsch which is the most common one and is carried out by the reaction of α-halo carbonyl compounds with thiourea or thioamids (Yavari et al, 2009;Ghodse & Telvekar, ,2015;Ayati, Emami, Asadipour, Shafiee, & Foroumadi, 2015).…”

mentioning

confidence: 99%

“…Despite the variety of mentioned methods for1,3-diazole and thiazole synthesis, several drawbacks have been reported which include high temperatures, long reaction time, low yields, the requirement of using toxic organic solvents and/or catalysts (Yavari et al, 2009;Narender, Reddy Somi, Sridhar, Nageswar, & Rao Rama, 2005).…”

mentioning

confidence: 99%

“…Ionic liquids (ILs) are defined as ionic salts with a melting point below 100°C, a high polarity and low vapor pressure (Yavari et al, 2009). These salts are formed of organic cation and inorganic anions (Ratti, 2014).…”

mentioning

confidence: 99%

See 4 more Smart Citations

Synthesis of Some Derivatives of 4-phenyl-1,3-dihydro-2H-imidazole-2-thion Using Ionic Liquid as Catalyst and Evaluation of Their Antimicrobial Activity

Behmaram¹,

Foroughifar²,

Foroughifar³

et al. 2017

IJC

View full text Add to dashboard Cite

The synthesis of some 1,3-diazoles and thiazoles was realized in different conditions: a) In the presence of PTSA or sulfuric acid as catalyst we obtained only diazole products(4 a-d ).b) In basic medium such as DABCO or sodium hydroxide and ionic liquid afforded thiazoles. c) Both products, diazoles and thiazoles were collected when using methanol as catalyst and solvent.All structures were confirmed by IR, 1 H NMR and 13 C NMR spectroscopy. The antibacterial activity of some synthesized compounds was investigated against Escherichia Coli (ATCC: 25922) and Serratia marcescens (ATCC: 13880) as gram negative bacteria, Bacillus sabtilis (ATCC: 6633) and Staphylococcus aureus (ATCC: 6338) as gram positive bacteria. Some of these products exhibit good activities to significant antibacterial activity.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Some Derivatives of 4-phenyl-1,3-dihydro-2H-imidazole-2-thion Using Ionic Liquid as Catalyst and Evaluation of Their Antimicrobial Activity

Behmaram¹,

Foroughifar²,

Foroughifar³

et al. 2017

IJC

View full text Add to dashboard Cite

show abstract

Synthesis in Green Solvents

Orha

Akien

Horváth

2012

Handbook of Green Chemistry

View full text Add to dashboard Cite

The sections in this article are The Role of Solvents in Synthesis Types of Solvent Atomic Liquids Molecular Liquids Ionic Liquids Solvent Polarity Protic Solvents Problems with Solvents Application of Green Solvents Water Fluorous Solvents Supercritical Carbon Dioxide Ionic Liquids Conclusion

show abstract

An Efficient One‐pot Synthesis of Aryl‐substituted 1‐(Thiazol‐2‐yl)‐1H‐pyrazole‐3‐carboxylates via a Hantzsch Synthesis‐Knorr Reaction Sequence

Zhai

Jiang

et al. 2014

Chin. J. Chem.

View full text Add to dashboard Cite

The treatment of α-bromoalkyl aryl ketones and 2-(propan-2-ylidene)hydrazine carbothioamide afforded 4-aryl-2-(2-(propan-2-ylidene)hydrazinyl)thiazoles via a Hantzsch-thiazole synthesis, which reacted with 4-aryl-2,4-diketoesters via a sequential Knorr-pyrazole reaction to deliver a variety of aryl-substituted ethyl 1-(thiazol-2-yl)-1Hpyrazole-3-carboxylates in a one-pot fashion with moderate to high yields. The key intermediates 4-aryl-2,4-diketoesters, existing as its enolic lithium salt, were synthesized in situ by a high-yield tert-BuOLi-mediated Claisen condensation of alkylphenones and diethyl oxalate. This class of elegant molecule comprises aryl groups on the two different heterocyclic cores, and the configurations of two representative molecules were determined by single crystal X-ray crystallography.

show abstract

A one-pot synthesis of functionalized ethyl 1,3-thiazole-5-carboxylates from thioamides or thioureas and 2-chloro-1,3-dicarbonyl compounds in an ionic liquid

Cited by 18 publications

References 14 publications

Synthesis of Some Derivatives of 4-phenyl-1,3-dihydro-2H-imidazole-2-thion Using Ionic Liquid as Catalyst and Evaluation of Their Antimicrobial Activity

Synthesis of Some Derivatives of 4-phenyl-1,3-dihydro-2H-imidazole-2-thion Using Ionic Liquid as Catalyst and Evaluation of Their Antimicrobial Activity

Synthesis in Green Solvents

An Efficient One‐pot Synthesis of Aryl‐substituted 1‐(Thiazol‐2‐yl)‐1H‐pyrazole‐3‐carboxylates via a Hantzsch Synthesis‐Knorr Reaction Sequence

Contact Info

Product

Resources

About