Microwave-assisted efficient synthesis of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl via 1,3-dipolar cycloaddition

Zheng, Rong; Feng, Fan; Zhang, Zhihui; Fu, Jiaxu; Su, Qing; Zhang, Yumin; Gu, Qiang

doi:10.1007/s11030-019-09973-0

Cited by 3 publications

(2 citation statements)

References 33 publications

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“…A competent preparation of 3‐substituted bis‐isoxazole ethers 3 done by 1,3‐dipolar cycloaddition reaction which has the reactant material 3‐substituted phenyl‐5‐((prop‐2‐yn‐1‐yloxy)methyl) isoxazoles 1 and (Z)‐2‐chloro‐n‐hydroxynicotinimidoyl chloride 2 in the presence of NaHCO 3 which act as an acid‐binding agent in THF solvent‐dissolved along with traces of water under catalyst‐free microwave‐assisted conditions [45]. The synthetic route and possible mechanism proposed by R. Zheng and his co‐worker has been depicted in Scheme 24.…”

Section: Synthetic Methods Of Isoxazole and Their Derivativesmentioning

confidence: 99%

“…S C H E M E 2 3 Preparation of 3-methyl-4-arylmethyleneisoxazol-5(4H)-ones under microwave radiation in presence of solvent-free conditions [44] S C H E M E 2 4 Synthesis of 3-substituted bis-isoxazole ethers derivatives using microwave radiation [45] (E, Z)-4-(3-Phenylisoxazol-5-yl)but-3-en-2-one 3 prepared by oxidative ring opening reaction of 2-(5-methylfuran-2-yl)-1-phenylethanone oxime 2, surveyed by iodine mediated isomerization as shown in Scheme 26. Oxime was formed using a reaction of furfuryl ketone 1 and hydroxylamine hydrochloride, with sodium acetate in the presence of ethanol.…”

Section: S C H E M E 2 2 Microwave-irradiation Technology For Synthes...mentioning

confidence: 99%

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A review of recent synthetic strategies and biological activities of isoxazole

Pandhurnekar¹,

Pandhurnekar

Mungole³

et al. 2022

Journal of Heterocyclic Chem

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Among different heterocyclic compounds, isoxazole and their analogues are very important classes of heterocyclic compounds as they display an extensive range of biological actions. This makes such scaffolds very important structures in the field of medicinal chemistry. From an extensive literature assessment, isoxazole is clinically proven to be very effective as an anti‐bacterial, anti‐fungal, anti‐inflammatory, anti‐cancer, anti‐tubercular, and anti‐neoplastic agent. The different derivatives of isoxazole which exhibits adjustment in their structure have shown a high degree of variety in their medicinal properties which makes evident them as very beneficial in the progress of novel bioactive drugs which show enhanced effectiveness along with minor harmfulness. Structural aspects of isoxazole having aromaticity with weaker nitrogen‐oxygen bonding provide a potential site for the ring cleavage. Thus, this isoxazole ring system allows easier modifications of substituents in their ring structure which consequently make isoxazole very useful intermediates in various synthetic routes of bioactive compounds. Hence, the synthesis and evaluation of isoxazole‐containing molecules with wider therapeutic consequences are always the topic of interest for chemists. Hence, in light of this comprehensive research on isoxazole, it is thought worthwhile to review various pathways for the synthesis of isoxazole analogues and having a broad spectrum of bioactive actions.

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Section: Synthetic Methods Of Isoxazole and Their Derivativesmentioning

confidence: 99%

Section: S C H E M E 2 2 Microwave-irradiation Technology For Synthes...mentioning

confidence: 99%

A review of recent synthetic strategies and biological activities of isoxazole

Pandhurnekar¹,

Pandhurnekar

Mungole³

et al. 2022

Journal of Heterocyclic Chem

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Green approaches for the synthesis of pharmacologically enviable isoxazole analogues: a comprehensive review

Basavanna

Doddamani²,

Chandramouli

et al. 2022

J IRAN CHEM SOC

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A Review on Green Synthesis and Biological Activities of Medicinally Important Nitrogen and Oxygen Containing Heterocycles

Gulati

Singh

Sangwan

2023

COC

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Recently, the application of green chemistry for the formation of potential bioactive heterocyclic moieties has turned out to be the key area of research for organic chemists due to the growing concern over environmental issues. Therefore, the development of nonhazardous synthetic protocols gained the particular attention of synthetic chemists as a frontier task in the present scenario. Nowadays, microbial infections have been haunting human civilization since prehistoric times, resulting in many deaths worldwide. Cancer is a fatal and dreadful disease without any appropriate cure, thus threatening humanity in both the developing and developed worlds. Therefore, there is a critical requirement for the design and synthesis of new classes of compounds to circumvent these diseases. Heterocycles are unique precursors for the synthesis of various pharmaceuticals and agrochemicals, particularly those possessing N- or O- moieties. The methods to prepare heterocycles are of great importance in synthesizing organic compounds, especially the heterocycles found in natural products. The synthesis of nitrogen and oxygen-containing heterocycles viz. Coumarins, dihydropyrimidinones, imidazoles, isoxazoles, and benzimidazoles represent attractive and demanding work for chemists as these molecules have found extensive applications in several fields, such as materials science, analytical chemistry and most importantly in, medicinal chemistry. In this review paper, we focus on the synthetic strategy to prepare these types of heterocyclic compounds by green methods and discuss their various biological applications.

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Microwave-assisted efficient synthesis of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl via 1,3-dipolar cycloaddition

Cited by 3 publications

References 33 publications

A review of recent synthetic strategies and biological activities of isoxazole

A review of recent synthetic strategies and biological activities of isoxazole

Green approaches for the synthesis of pharmacologically enviable isoxazole analogues: a comprehensive review

A Review on Green Synthesis and Biological Activities of Medicinally Important Nitrogen and Oxygen Containing Heterocycles

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