A facile, solvent and catalyst free, microwave assisted one pot synthesis of hydrazinyl thiazole derivatives

Chinnaraja, D.; Rajalakshmi, R.

doi:10.1016/j.jscs.2014.05.001

Cited by 24 publications

(11 citation statements)

References 18 publications

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“…Synthesis of thiazoles from thiocarbohydrazide, aldehydes, and α-bromoketones under microwave irradiation. Chinnaraja and Rajalakshmi [45] reported the microwave-assisted synthesis of novel hydrazinyl thiazole derivatives within 30-175 s under solvent-and catalyst-free conditions. Starting from either various carbonyl compounds, thiosemicarbazide, and alpha-haloketones or substituted thiosemicarbazones and alpha-haloketones (Scheme 14), the target compounds were obtained in good to excellent yield and high purity through an eco-friendly, one-pot procedure.…”

Section: Synthesis Of Thiazole Derivativesmentioning

confidence: 99%

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

et al. 2021

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Thiazole, a five-membered heteroaromatic ring, is an important scaffold of a large number of synthetic compounds. Its diverse pharmacological activity is reflected in many clinically approved thiazole-containing molecules, with an extensive range of biological activities, such as antibacterial, antifungal, antiviral, antihelmintic, antitumor, and anti-inflammatory effects. Due to its significance in the field of medicinal chemistry, numerous biologically active thiazole and bisthiazole derivatives have been reported in the scientific literature. The current review provides an overview of different methods for the synthesis of thiazole and bisthiazole derivatives and describes various compounds bearing a thiazole and bisthiazole moiety possessing antibacterial, antifungal, antiprotozoal, and antitumor activity, encouraging further research on the discovery of thiazole-containing drugs.

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Section: Synthesis Of Thiazole Derivativesmentioning

confidence: 99%

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

et al. 2021

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“…Here we have shown different reaction strategies developed by different research groups for the synthesis of hydrazinyl thiazoles. Some of them are catalyst-free, [38,39] some are both catalyst and solvent-free, [40,41] while some are catalyzed by homogeneous, [17,[42][43][44][45][46][47][48][49][50] and heterogeneous [51][52][53][54] catalysts. All the processes have some advantages over each other and also have some limitations.…”

Section: Discussionmentioning

confidence: 99%

“…In 2014 Chinnaraja et al . reported [40] a solvent and catalyst‐free one‐pot synthesis of hydrazinyl thiazoles under Microwave irradiation. In this method, aryl ketones 17 and 20 , thiosemicarbazide 10 and substituted phenacyl bromides 18 react in an one‐pot protocol under 300 W microwave irradiation (MWI) for a time period of 30–175 sec to produce hydrazinyl thiazole derivatives 19 and 21 , respectively (Scheme 5a and 5b).…”

Section: Synthetic Developmentsmentioning

confidence: 99%

Synthetic Strategies for Hydrazinyl Thiazole Derivatives

2020

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Hydrazinyl thiazole is frequently encountered in natural as well as in synthetic compounds. It is also an important pharmacophore and has some other useful applications. In this review article, we have compiled different green synthetic procedures for the synthesis of hydrazinyl thiazole derivatives. Also, the critical analysis of different synthetic schemes will help to understand the lacks in developed procedures and to develop new methodologies regarding its synthesis, specially using heterogeneous organocatalyst and photocatalyst.

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“…The first method employs a two-step condensationcyclization sequence between a carbonyl function and thiosemicarbazide to yield thiosemicarbazone, which is then cyclized with α-halo carbonyl compound to produce hydrazinyl thiazole derivatives. In current literature, Reddys, [9] Mokhtary, [10] Hangirgekar, [11] Kannan, [12] Chobe, [13] Chinnaraja, [14] Bhosale, [15] and Iqbal [16] have demonstrated the rapid synthesis of the hydrazinyl thiazole motif utilizing various catalytic models.…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free One‐Pot Synthesis of 2‐(2‐Hydrazinyl) Thiazole Derivatives Using Graphene Oxide in a Green Solvent and Molecular Docking Studies

et al. 2021

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An efficient, one-pot three-component reaction in the synthesis of a wide range of 2,4-disubstituted hydrazinyl thiazole scaffolds in ethanol at room temperature has been developed by the reaction of carbonyl compounds, phenacyl bromides, and thiosemicarbazide, using graphene oxide (GO) as a catalyst. The present catalytic method has many significant advantages such as shorter reaction time, broad substrate scope, low catalyst loading, environmentally benign solvent media, easy handling, and operational simplicity at room temperature. The products are identified based on their various spectroscopic data. The GO catalyst has a high reusability rate and is simple to recover. A mechanistic study suggests that the reaction takes place via a thiosemicarbazone intermediate, which is isolated and confirmed in this study using spectroscopic techniques. Thereafter, a molecular docking study has been performed to evaluate the binding affinity of hydrazinyl thiazole derivative as a possible inhibitor on the protein active site of human α-amylase and glucosamine 6-phosphate synthase[a] A

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A facile, solvent and catalyst free, microwave assisted one pot synthesis of hydrazinyl thiazole derivatives

Cited by 24 publications

References 18 publications

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

An Overview of the Synthesis and Antimicrobial, Antiprotozoal, and Antitumor Activity of Thiazole and Bisthiazole Derivatives

Synthetic Strategies for Hydrazinyl Thiazole Derivatives

Metal‐Free One‐Pot Synthesis of 2‐(2‐Hydrazinyl) Thiazole Derivatives Using Graphene Oxide in a Green Solvent and Molecular Docking Studies

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