Cu(I)-Catalyzed Three-Component Cyclization for the Construction of Functionalized Thiazoles

Wang, Yajun; Liu, Xiang; Zhu, Baofu; Guo, Peijun; Pei, Yongyan; He, Qiuxing; Cao, Hua

doi:10.1021/acs.joc.0c01381

Cited by 18 publications

(9 citation statements)

References 60 publications

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“…A series of functionalized thiazoles were efficiently prepared from thioamides, ynals, and alcohols through Cu( i )-catalyzed reaction. 21 Multiple bonds including C–S, C–N, and C–O were formed in this one pot reaction and 5 mol% CuBr(PPh 3 ) 3 was used as the catalyst. Several acids including PivOH, MsOH, PhCO 2 H, TsOH were screened and the best results were offered by PivOH.…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

2021

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Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

2021

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

confidence: 99%

“…In 2020, Cao et al presented a novel and straightforward strategy for the synthesis of decorated thiazoles starting from thioamides 106, ynals 107, and alcohols via a Cu(I)-catalyzed reaction (Scheme 46) [118]. Simple aldehydes 110, amines 87, and elemental sulfur can be employed to construct thiazoles through an oxidative sulfuration/cyclization pathway.…”

Section: Miscellaneous Metal-catalyzed Heterocycle Synthesis Approachesmentioning

confidence: 99%

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

2021

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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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“…19 Synthesis of trisubstituted thiazoles from the reaction of alkyne and thioamide in the presence of organo-photocatalyst and blue light has been reported recently (Scheme 1, eq c). 20 Similarly, the reaction of propargyl aldehyde, thioamide, and alcohols in the presence of pivalic acid and copper catalyst provided three-component products as shown in Scheme 1, eq d. 21 Very recently, Illa and co-workers have developed an efficient method for the synthesis of substituted thiazoles from cyanamide as shown in Scheme 1, eq e. 22 Although many methods are known for the synthesis of substituted thiazoles, still there is no report on one-pot multicomponent reactions for the synthesis of thiazole−indole hybrids. We have also extended this multicomponent strategy for the synthesis of structurally interesting bis-thiazoles having a benzoquinone linker and novel thiazole-containing polymers.…”

Section: ■ Introductionmentioning

confidence: 99%

Multicomponent Synthesis of Fluorescent Thiazole–Indole Hybrids and Thiazole-Based Novel Polymers

et al. 2022

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Herein, we report an efficient multicomponent reaction for the synthesis of trisubstituted thiazoles involving a one-pot C–C, C–N, and C–S bond-forming process from the readily available starting materials. The reaction of arylglyoxal, indole, and aryl thioamides in the acetic acid medium under sealed heating conditions provided 3-(2,4-diarylthiazol-5-yl)-1H-indoles (4) in good to excellent yields. Using a similar reaction strategy, the reaction of arylglyoxal, aryl thioamide, and 2,5-dihydroxy-1,4-benzoquinone provided structurally interesting bis-thiazoles having dihydroxy-1,4-benzoquinone linker (9). All of the products were fully characterized by spectroscopic techniques. We also recorded single-crystal X-ray diffraction (XRD) of compounds 4b and 9a for unambiguous structure determination. Indole-linked trisubstituted thiazoles (4) exhibit prominent fluorescence properties. The relative fluorescence quantum yields of all of the thiazole-linked indoles were measured in the dimethyl sulfoxide (DMSO) medium with respect to quinine sulfate in 0.1 M H2SO4 as reference. The scope of this reaction was further explored by preparing novel polymers 11a and 11b using naphthalene/benzene-1,4-bis(carbothioamide) in multicomponent polymerization.

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Cu(I)-Catalyzed Three-Component Cyclization for the Construction of Functionalized Thiazoles

Cited by 18 publications

References 60 publications

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

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

Multicomponent Synthesis of Fluorescent Thiazole–Indole Hybrids and Thiazole-Based Novel Polymers

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