An improved protocol for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones through L-valine-mediated domino three-component strategy

Kour, Parteek; Ahuja, Monika; Sharma, Pratibha; Kumar, Ashok; Kumar, Anil

doi:10.1007/s12039-020-01801-5

Cited by 13 publications

(3 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Kumar et al described a metal-free, L-valine-promoted domino multicomponent cyclocondensation reaction in which alkylacetoacetates 171, hydroxylamine hydrochloride, and aldehydes 1 were reacted in ethanol under reflux for 4 minutes to synthesize isoxazolone derivatives 172 (Scheme 32). [48] At first, the reaction between alkylacetoacetate 171 and hydroxylamine hydrochloride in the presence of L-valine to afford the anticipated oxime 173. the oxime 173 then react with aldehyde 1 generate intermediate 174 which followed by an intramolecular reaction between hydroxyl and carbonyl groups formed intermediate 176 with the elimination of H 2 O.…”

Section: Synthesis Of Oxazoles and Isoxazolesmentioning

confidence: 99%

See 1 more Smart Citation

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

et al. 2023

View full text Add to dashboard Cite

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.

show abstract

Section: Synthesis Of Oxazoles and Isoxazolesmentioning

confidence: 99%

“…described a metal‐free, L‐valine‐promoted domino multicomponent cyclocondensation reaction in which alkylacetoacetates 171 , hydroxylamine hydrochloride, and aldehydes 1 were reacted in ethanol under reflux for 4 minutes to synthesize isoxazolone derivatives 172 (Scheme 32). [48] …”

Section: Five‐membered Heterocyclic Compoundsmentioning

confidence: 99%

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

et al. 2023

View full text Add to dashboard Cite

show abstract

“…Notably, 4-arylmethylneisoxazol-5(4H)-ones are very useful synthetic intermediates of various applied heterocycles such as pyridopyrimidines 8 , 4-arylpyrrolidones, 1,3-oxazine-6-ones 9 , nicotinates 10 , β-alkylated γ-functionalized ketones 11 and, α-aminopyrrole derivatives 12 . Therefore, these structures have interested organic chemists, and a review of the literature shows a wide variety of homogenous and heterogeneous catalysts and techniques such as sodium acetate 13 , DABCO 14 , modified-MMT 15 , Cu/TCH-pr@SBA-15 16 , L-valine 17 , ZSM-5 18 , DES (ChCl/Gly) 19 , ultrasonic irradiation 20 , Sn(II)-MMT 21 , and ionic liquids 22 . These include the cyclization of O-propioloyl oxime via intermolecular arylidene group transfer 23 , the condensation of 3-phenylisoxazol-5-one within aryl halide, the reaction of 1,3-dicarbonyl compounds with benzaldoximes, and condensation of hydroxylamine with β-keto esters.…”

Section: Introductionmentioning

confidence: 99%

A green protocol for the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using modified β-cyclodextrin as a catalyst

Tajbakhsh

Naimi‐Jamal

Saeed

et al. 2022

Sci Rep

View full text Add to dashboard Cite

This manuscript reports an impressive and facile strategy for synthesizing isoxazole derivatives using immobilized Cu (I) in metformin-functionalized β-cyclodextrin as a catalyst. The architecture of this catalyst was characterized by different analytical techniques such as Fourier transform infrared spectroscopy, Thermogravimetric analysis, X-ray diffraction, Field emission scanning electron microscopy, and Energy-dispersive X-ray spectroscopy. The catalyst showed remarkable reusability even after 7 consecutive runs.

show abstract

Dipolarophile‐Steered Formal Stereodivergent Synthesis of 2,5‐cis/trans‐Pyrrolidines Based on Asymmetric 1,3‐Dipolar Cycloaddition of Imino Lactones

Furuya,

Muroi,

Kanemoto

et al. 2023

Chemistry A European J

View full text Add to dashboard Cite

The stereodivergent asymmetric synthesis of 2,5‐trans/cis pyrrolidines by 1,3‐dipolar cycloaddition using two different types of activated alkenes is described. When ylidene‐isoxazolones were employed as dipolarophiles, the Ag/(S,Sp)‐iPr‐FcPHOX‐catalyzed asymmetric [3+2] cycloaddition of imino lactones proceeded with 2,5‐trans selectivity. Subsequent decarboxylation of the isoxazolone rings produced pyrrolidines with 2,5‐trans stereoretention. In the reaction using acyclic enones as activated alkenes, the Ag/(R,Sp)‐ThioClickFerrophos complex‐catalyzed asymmetric [3+2] cycloaddition afforded 2,5‐cis substituted pyrrolidines in high yields and enantioselectivities. Therefore, these methods can be considered as a formal stereodivergent synthesis of 2,5‐cis/trans pyrrolidines.

show abstract

An improved protocol for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones through L-valine-mediated domino three-component strategy

Cited by 13 publications

References 32 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

A green protocol for the one-pot synthesis of 3,4-disubstituted isoxazole-5(4H)-ones using modified β-cyclodextrin as a catalyst

Dipolarophile‐Steered Formal Stereodivergent Synthesis of 2,5‐cis/trans‐Pyrrolidines Based on Asymmetric 1,3‐Dipolar Cycloaddition of Imino Lactones

Contact Info

Product

Resources

About