Catalyst-Free Synthesis of Polysubstituted 5-Acylamino-1,3-Thiazoles via Hantzsch Cyclization of α-Chloroglycinates

Tomassetti, Mara; Lupidi, Gabriele; Piermattei, Pamela; Rossi, Federico Vittorio; Lillini, Samuele; Bianchini, Gianluca; Aramini, Andrea; Ciufolini, Marco A.; Marcantoni, Enrico

doi:10.3390/molecules24213846

Cited by 9 publications

(6 citation statements)

References 51 publications

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“…These catalyzed cyclizations have proved to be particularly useful methodologies for the construction of 1,3-thiazoles structures in the pharmaceutical industry, where they have enabled the straightforward diversification of lead heterocycles, and thereby facilitated drug development. In the context of green chemistry, today there is an increasing interest in synthetic approaches in the absence of catalysts, thus we developed a Hantzsch cyclization to 1,3-thiazoles that involves the study of starting materials in order to allow processes without catalysts [46].…”

Section: Resultsmentioning

confidence: 99%

The Appropriate Acyclic Precursors to Build Biologically Active 5-acylamino-1,3-thiazoles

Tomassetti

Lupidi

Gabrielli

et al. 2021

Current Advances in Chemistry and Biochemistry Vol. 8

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The aim of this opinion article is to highlight the trends in the development of efficient catalyst-free synthesis of the Hantzsch polysubstituted 1,3-thiazoles. They are heterocycles of particular importance in the pharmaceutical industry, and the strategy involves the cyclization reaction of acyclic precursors with minimum auxiliary substances, toxic reagents, organic solvents, and disposal problems.

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Section: Resultsmentioning

confidence: 99%

The Appropriate Acyclic Precursors to Build Biologically Active 5-acylamino-1,3-thiazoles

Tomassetti

Lupidi

Gabrielli

et al. 2021

Current Advances in Chemistry and Biochemistry Vol. 8

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“…Hantzsch construction of thiazole derivatives (2.6) was established by the reaction of α-chloroglycinate esters with thioamides or thioureas. Targeted compounds are obtained from readily available and inexpensive building blocks through an environmentally benign process and without catalysts [50] ( Figure 10).…”

Section: Miscellaneous Methodsmentioning

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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“…In the next section, we report current synthetic methodologies to yield substituted thiazoles and nonaromatic isatins. In the last few years, innovative and valid metal/additive-free approaches have been developed for the synthesis of these heterocycles [ 117 ]. In this work, we focus our attention on metal-triggered processes.…”

Section: Sars-cov-2 3cl Protease Target Drugsmentioning

confidence: 99%

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

2021

Self Cite

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The outbreak of SARS-CoV-2 has drastically changed our everyday life and the life of scientists from all over the world. In the last year, the scientific community has faced this worldwide threat using any tool available in order to find an effective response. The recent formulation, production, and ongoing administration of vaccines represent a starting point in the battle against SARS-CoV-2, but they cannot be the only aid available. In this regard, the use of drugs capable to mitigate and fight the virus is a crucial aspect of the pharmacological strategy. Among the plethora of approved drugs, a consistent element is a heterocyclic framework inside its skeleton. Heterocycles have played a pivotal role for decades in the pharmaceutical industry due to their high bioactivity derived from anticancer, antiviral, and anti-inflammatory capabilities. In this context, the development of new performing and sustainable synthetic strategies to obtain heterocyclic molecules has become a key focus of scientists. In this review, we present the recent trends in metal-promoted heterocyclization, and we focus our attention on the construction of heterocycles associated with the skeleton of drugs targeting SARS-CoV-2 coronavirus.

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Catalyst-Free Synthesis of Polysubstituted 5-Acylamino-1,3-Thiazoles via Hantzsch Cyclization of α-Chloroglycinates

Abstract: A catalyst-free heterocyclization reaction of α-chloroglycinates with thiobenzamides or thioureas leading to 2,4-disubstituted-5-acylamino-1,3-thiazoles has been developed. The methodology provides straightforward access to valuable building blocks for pharmaceutically relevant compounds.

Cited by 9 publications

References 51 publications

The Appropriate Acyclic Precursors to Build Biologically Active 5-acylamino-1,3-thiazoles

The Appropriate Acyclic Precursors to Build Biologically Active 5-acylamino-1,3-thiazoles

Synthesis and Biological Evaluation of Thiazole Derivatives

Metal-Promoted Heterocyclization: A Heterosynthetic Approach to Face a Pandemic Crisis

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