Transition Metal‐ and Oxidant‐Free Regioselective Synthesis of 3,4,5‐Trisubstituted Pyrazoles by Means of [3+2] Cycloaddition Reactions

Allaka, Bhargava Sai; Basavoju, Srinivas; Krishna, G. Rama

doi:10.1002/slct.202200605

Cited by 6 publications

(3 citation statements)

References 45 publications

(34 reference statements)

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“…Allakaet al reported the regioselective synthesis of 3,4,5trisubstituted pyrazole derivatives 315 via [3 + 2] cycloaddition reaction (Scheme 59). [77] This MCR was performed by reacting thiazolidinedione chalcones 314, benzaldehydes 1 and Ntosylhydrazinein presence of Cs 2 CO 3 in DMF at 100 °C. Under mild reaction condition the reaction proceeds through CÀ C and CÀ N bond formations and produced structurally diverse pyrazole derivatives 315 in moderate to good yields.…”

Section: Synthesis Of Pyrazolesmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Section: Synthesis Of Pyrazolesmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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“…37–41 Here in, we report ionic liquid mediated and ultrasound assisted, one-pot multicomponent synthesis of 1,3-diphenylpyrazole- based spirooxindolopyrrolizidines via [3+2]-cycloaddition and their in vitro anti-TB activity. 42,43…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-assisted ionic liquid-mediated green method for synthesis of 1,3-diphenylpyrazole-based spirooxindolopyrrolizidines, their anti-tubercular activity, molecular docking study and ADME predictions

Baddepuri,

Gamidi,

Kumari

et al. 2024

New J. Chem.

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“…The [3+2] cycloaddition process is a highly regio-selective approach for the synthesis of spiroxindoles. 12,13,14,15 Spirooxindole alkaloids found in nature, such as horsfiline, extracted from Horsfieldia superba are used in traditional medicine (Figure 1). 16,17 However, the spiroxindoles having 1,2,4-oxadiazole ring systems are rare in the literature.…”

Section: Introductionmentioning

confidence: 99%

An ultrasound assisted synthesis of spirooxindolo-1,2,4-oxadiazoles via [3+2] cycloaddition reaction and their anti-cancer activity

Basavoju¹,

Kanchrana²,

Allaka³

et al. 2023

Arkivoc

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A facile and ultrasound assisted green methodology was adopted to achieve spirooxindolo-1,2,4-oxadiazoles via a [3+2] cycloaddition of aryl nitrile oxides and isatin Schiff bases at room temperature with good yields and lesser reaction times. The proposed procedure avoids traditional column chromatography resulting in good to excellent yields. The synthesized compounds were evaluated for their anti-cancer activity against SK-OV-3, HeLa, HCT-116, DU-145, A549 and HEK-293 cell lines. Two of them showed significant anti-cancer activity against HeLa with IC50 value 10.75±0.39 µM and 12.43±0.77 µM respectively. In vitro anti-cancer activity X-ray structure Molecular docking Good yields up to 85% Less reaction time Column chromatography free

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Transition Metal‐ and Oxidant‐Free Regioselective Synthesis of 3,4,5‐Trisubstituted Pyrazoles by Means of [3+2] Cycloaddition Reactions

Cited by 6 publications

References 45 publications

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Ultrasound-assisted ionic liquid-mediated green method for synthesis of 1,3-diphenylpyrazole-based spirooxindolopyrrolizidines, their anti-tubercular activity, molecular docking study and ADME predictions

An ultrasound assisted synthesis of spirooxindolo-1,2,4-oxadiazoles via [3+2] cycloaddition reaction and their anti-cancer activity

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