Highly efficient microwave-assisted one-pot synthesis of 4-aryl-2-aminothiazoles in aqueous medium

Wagare, Devendra S.; Netankar, Prashant D.; Shaikh, Melad; Farooqui, Mazahar; Durrani, Ayesha

doi:10.1007/s10311-017-0619-1

Cited by 40 publications

(13 citation statements)

References 25 publications

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“…Thiazoles are employed in many medicinally important drugs (Figure 14) such as sulfathiazole (186), abafungin (187) and ritonavir (188) [156]. In 2017, Wagare and co-workers [157] demonstrated the construction of substituted thiazole ring 190 by utilizing a three-component reaction involving NBS (189), aromatic ketones 103 and thioureas 77 under microwave radiation using PEG-400 and water as a medium at 80-85 °C (Scheme 79).…”

Section: Thiazolesmentioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

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Microwave-assisted (MWA) multicomponent reactions (MCRs) have successfully emerged as one of the useful tools in the synthesis of biologically relevant heterocycles. These reactions are strategically employed for the generation of a variety of heterocycles along with multiple point diversifications. Over the last few decades classical MCRs such as Ugi, Biginelli, etc. have witnessed enhanced yield and efficiency with microwave assistance. The highlights of MWA-MCRs are high yields, reduced reaction time, selectivity, atom economy and simpler purification techniques, such an approach can accelerate the drug discovery process. The present review focuses on the recent advances in MWA-MCRs and their mechanistic insights over the past decade and shed light on its advantage over the conventional approach.

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Section: Thiazolesmentioning

confidence: 99%

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Gulati¹,

John²,

Shankaraiah³

2021

Beilstein J. Org. Chem.

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“…Such strategy simplifies the synthetic procedure, reduces time and energy necessary for the reaction comparing to multi-step procedures. Such one-pot processes are very convenient methodology for the synthesis of biologically relevant heterocycles, while it enables the synthesis of the complex scaffolds from simple molecules in a single process (Wagare et al 2015;Baharfar et al, 2018;Das Sharma et al 2008;Kidwai and Mothsra 2006). According to our knowledge, such products have never been obtained in single step, so we have established the first example of one-pot procedure for the synthesis of 3-cyanopiperidin-2,6-dione derivatives.…”

Section: Introductionmentioning

confidence: 99%

Environmental-friendly one-pot cascade synthesis of 3-cyanopiperidin-2,6-diones

2019

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3-Cyanopiperidin-2,6-diones are key intermediates in the synthesis of several drugs and natural products. We developed onepot synthesis of 3-cyanopiperidin-2,6-diones by Knoevenagel condensation of cyanoacetic acid and aldehydes, followed by addition of cyanoacetic acid, Achmatowicz reaction and decarboxylation. We tested a wide range of aliphatic and aromatic aldehydes. Products were obtained under simple, environmentally friendly conditions and in yields up to 99%. Substrates were stirred in toluene at reflux, and filtered through short pad of silica gel, and the product was purified by recrystallization.

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“…As a part of our ongoing program in the development of environmentally benign and sustainable process , herein, we wish to report a straightforward one‐pot three‐component reaction of substituted isatin, active methylene group, and 4‐hydroxycoumarin in γ‐valerolactone for the synthesis of spirooxindoles with fused pyrano[3,2‐ c ]chromene derivatives. To the best of our knowledge, there is no report available in the literature for the synthesis of spirooxindoles with fused pyrano[3,2‐ c ]chromene derivatives using γ‐valerolactone as green and reusable bio‐based solvent (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

γ‐Valerolactone as a Promising Bio‐Compatible Media for One‐Pot Synthesis of Spiro[indoline‐3,4'‐pyrano[3,2‐c]chromene Derivatives

Diwan¹,

Farooqui²

2018

Journal of Heterocyclic Chem

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A general, highly efficient, and green protocol for the synthesis of biologically important spiro[indoline-3,4 0 -pyrano[3,2-c]chromene derivatives is developed by one-pot, three-component approach involving substituted isatin, active methylene group, and 4-hydroxy coumarin. This report describes the use of γvalerolactone as a green reaction media for a variety of substrates. The advantageous features of this methodology are the environmentally benign character, operational simplicity, high yield processing (91-96%), easy handling, and the reaction medium can be recycled and reused several times without significant loss of its efficiency. White solid;Scheme 3. Plausible mechanism of spiro[indoline-3,4 0 -pyrano[3,2-c]chromene derivatives 4a-q. [Color figure can be viewed at wileyonlinelibrary.com] 2820 F. Diwan and M. Farooqui

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Highly efficient microwave-assisted one-pot synthesis of 4-aryl-2-aminothiazoles in aqueous medium

Cited by 40 publications

References 25 publications

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

Environmental-friendly one-pot cascade synthesis of 3-cyanopiperidin-2,6-diones

γ‐Valerolactone as a Promising Bio‐Compatible Media for One‐Pot Synthesis of Spiro[indoline‐3,4'‐pyrano[3,2‐c]chromene Derivatives

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