Intramolecular nucleophilic substitution at an sp2 carbon: synthesis of substituted thiazoles and imidazole-2-thiones

Shen, Shusu; Lei, Mao-Yi; Wong, Yun-Xuan; Tong, Mun-Ling; Teo, Priscilla Lu-Yi; Chiba, Shunsuke; Narasaka, Koichi

doi:10.1016/j.tetlet.2008.12.118

Cited by 20 publications

(9 citation statements)

References 20 publications

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“…The lonely pair of electrons in the sulfur atom of the thiazole ring is dislocated, which meets the Huckel rule condition for a minimum of six pi (π) electrons [2]. Thiazole undergoes various reactions such as donor-acceptor [3], intramolecular nucleophilic substitution [4], photochemical reaction [5,6], arylation [7], cycloaddition [8], oxidation [9], transformation [10], dimerization [11], etc. Some old but important methods for the production of thiazole rings include Hantzsch thiazole synthesis [12,13], Cook-Heilbron synthesis [14], Herz synthesis [15], modified Hantzsch synthesis [16], etc.…”

Section: Introductionmentioning

confidence: 94%

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Arshad¹,

Alam

Alshammari

et al. 2022

Molecules

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For many decades, the thiazole moiety has been an important heterocycle in the world of chemistry. The thiazole ring consists of sulfur and nitrogen in such a fashion that the pi (π) electrons are free to move from one bond to other bonds rendering aromatic ring properties. On account of its aromaticity, the ring has many reactive positions where donor–acceptor, nucleophilic, oxidation reactions, etc., may take place. Molecules containing a thiazole ring, when entering physiological systems, behave unpredictably and reset the system differently. These molecules may activate/stop the biochemical pathways and enzymes or stimulate/block the receptors in the biological systems. Therefore, medicinal chemists have been focusing their efforts on thiazole-bearing compounds in order to develop novel therapeutic agents for a variety of pathological conditions. This review attempts to inform the readers on three major classes of thiazole-bearing molecules: Thiazoles as treatment drugs, thiazoles in clinical trials, and thiazoles in preclinical and developmental stages. A compilation of preclinical and developmental thiazole-bearing molecules is presented, focusing on their brief synthetic description and preclinical studies relating to structure-based activity analysis. The authors expect that the current review may succeed in drawing the attention of medicinal chemists to finding new leads, which may later be translated into new drugs.

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Section: Introductionmentioning

confidence: 94%

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Arshad¹,

Alam

Alshammari

et al. 2022

Molecules

View full text Add to dashboard Cite

show abstract

“…Thiazoles holding a variability of substituents such as aliphatic, aromatic, heterocyclic, or alkenyl groups can be synthesized by an intramolecular nucleophilic substitution reaction of N-(2-bromoprop-2-enyl)thioamides [58]. This vinylic substitution technique would afford an exclusive synthetic method for a range of heterocycles.…”

Section: Thiazoles From Vinyl Bromidementioning

confidence: 99%

“…It has been projected that the sum of potential compounds with molecular weight of lower than 500 Da is 10 200 , where only 10 60 may retain drug-like applications. The percentage of molecules prepared untill today has been projected as one part in 10 58 or approximately the fraction of the mass of the proton to the mass of the sun. The concern is, therefore, the selection of new molecules from this vast universe that have the potential to be biologically active [4].…”

Section: Introductionmentioning

confidence: 99%

Significance of Thiazole-based Heterocycles for Bioactive Systems

Pola¹

2016

Scope of Selective Heterocycles From Organic and Pharmaceutical Perspective

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Monocyclic and Bicyclic aromatic heterocycles such as imidazoles, thiazoles, thiadiazoles, oxazoles, oxadiazoles quinazolines, indoles, benzimidazoles, purines pyrido[4,3-d]pyrimidines, thiazolo[5,4-d]pyrimidines, thiazolo[4,5-d]pyrimidines, oxazolo[5,4-d]pyrimidines and thieno[2,3-d]pyrimidines are renowned pharmacophores in drug discovery. These special structures are well explained and exemplified in chemical compound libraries. In this chapter, several types of thiazole based heterocyclic scaffolds such as monocyclic or bicyclic systems synthesis and their biological activities studies are presented, which are not frequently present in books and reviews. We mention the first importance of synthetic route of various thiazole based compounds and their applications in medicinal chemistry in this chapter.

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“…主要讨论了乙烯基卤代物的分子内亲核取代反应, 并成功地将此类分子内 S N V 反应应用到了很多杂环化合物的合成中, 其中包括五元杂环、四元杂环以及六元杂环等. 为了研究其他的类型的硫亲核试剂, 作者设计合成了分子内含有酰胺基团的 2-溴乙烯基类化合物 10 [19] . …”

Section: 乙烯基碳上的分子内亲核取代反应的研究unclassified

Nucleophilic Substitution Reactions at Vinylic Carbons

Shen¹

2014

Chin. J. Org. Chem.

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Intramolecular nucleophilic substitution at an sp2 carbon: synthesis of substituted thiazoles and imidazole-2-thiones

Cited by 20 publications

References 20 publications

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Thiazole: A Versatile Standalone Moiety Contributing to the Development of Various Drugs and Biologically Active Agents

Significance of Thiazole-based Heterocycles for Bioactive Systems

Nucleophilic Substitution Reactions at Vinylic Carbons

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