Solvent-free synthesis of 2-amino-4-arylthiazoles under microwave irradiation

Cáceres-Castillo, David; Carballo, Rubén M.; Tzec-Interián, Jorge A.

doi:10.1016/j.tetlet.2012.05.093

Cited by 25 publications

(17 citation statements)

References 32 publications

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“…The thiazole core was synthesized following Hantzsch's modified method reported before and shown in Scheme 1 [29]. The rapid and efficient solvent-free reaction of p-substituted acetophenones with thiourea and iodine under microwave irradiation led to 2-amino-4-arylthiazoles (1a-g).…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

2-Amino-4-arylthiazole Derivatives as Anti-giardial Agents: Synthesis, Biological Evaluation and QSAR Studies

et al. 2015

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A series of seven 2-amino-4-arylthiazoles were prepared following Hantzsch's modified method under microwave irradiation. A set of 50 derivatives was obtained and the in vitro activity against Giardia intestinalis was evaluated. The results on the biological activity revealed that, in general, the N-(5-bromo-4-arylthiazol-2-yl)-acetamide scaffold showed high bioactivity. In particular, compounds 6e (IC 50 = 0.39 μM) and 6b (IC 50 = 0.87 μM) were found to be more potent than the positive control metronidazole. Citoxicity and acute toxicity tests performed showed low toxicity and high selectivity of the most active compounds (6e SI = 139, 6b SI = 52.3). A QSAR analysis was applied to a data set of 37 obtained 2-amino-4-arylthiazoles derivatives and the best model described a strongly correlation between the anti-giardiasic activity and molecular descriptors as E2M, RDF115m, F10, MATS6v, and Hypnotic-80, with high statistical quality. This finding indicates that N-substituted aminothiazole scaffold should be investigated for the development of highly selective anti-giardial agent.

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Section: Synthesis Of Thiazolesmentioning

confidence: 99%

2-Amino-4-arylthiazole Derivatives as Anti-giardial Agents: Synthesis, Biological Evaluation and QSAR Studies

et al. 2015

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“…To overcome these shortcomings, eco-friendly methods as microwave irradiation technique are commonly used for synthesis of thiazole derivatives [45]. Rapid and elegant synthesis of a series of thiazoles (2.5.1) uses microwave heating under solvent-free conditions [32,46,47] (Figure 7).…”

Section: Using Microwave-assisted Synthesis (Maos)mentioning

confidence: 99%

Synthesis and Biological Evaluation of Thiazole Derivatives

Ibrahim¹,

Rizk²

2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Thiazoles belong to the group of azole heterocycles. They are aromatic five-membered heterocycles containing one sulfur and one nitrogen atom. In recent years thiazoles, their derivatives, and isomers have gained considerable attention because of their broad applications in different fields, such as agrochemicals, industrial, and photographic sensitizers. Also, they have pharmaceutical and biological activities that include antimicrobial (sulfazole), antiretroviral (ritonavir), antifungal (abafungin), anticancer (tiazofurin), antidiabetic, anti-inflammatory, anti-Alzheimer, antihypertensive, antioxidant, and hepatoprotective activities. The compounds containing thiazole moieties are a prominent structural feature in a variety of natural products, such as vitamin B and penicillin. Thus, in this chapter several types of thiazole-based heterocyclic scaffolds such as monocyclic or bicyclic systems synthesis and their biological activities studies are presented. Furthermore modification of thiazole-based compounds at different positions to generate new molecules with potent antitumor, antioxidant, and antimicrobial activities is described.

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“…Gonzalo et al [93] developed a one-pot solvent-free procedure for the synthesis of 2-amino-4-arylthiazoles 66 by the reaction of p-substituted acetophenones with thiourea and iodine under microwave irradiation (Scheme 10.48). …”

Section: Thiazolesmentioning

confidence: 99%

Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds

Dandia

Gupta

Maheshwari

2014

Green Chemistry: Synthesis of Bioactive Heterocycles

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The synthetic uses of molecular iodine are described. This chapter discusses the versatile uses of iodine in heterocyclic synthesis. Iodine is a universal oxidizing agent, a mild and nontoxic Lewis acid catalyst, and it catalyzes various organic reactions with high efficiency and selectivity. Also, iodine acts as an electrophile-nucleophile dual activator in the reactions. Further applications are the introduction of protecting groups, deprotection, iodocyclization, C-C bond formation, and formation of heterocycles. It is quite clear from the growing number

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Solvent-free synthesis of 2-amino-4-arylthiazoles under microwave irradiation

Cited by 25 publications

References 32 publications

2-Amino-4-arylthiazole Derivatives as Anti-giardial Agents: Synthesis, Biological Evaluation and QSAR Studies

2-Amino-4-arylthiazole Derivatives as Anti-giardial Agents: Synthesis, Biological Evaluation and QSAR Studies

Synthesis and Biological Evaluation of Thiazole Derivatives

Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds

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