An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4<i>H</i>)-ones in Aqueous Medium

Chavan, Abhijit P.; Pinjari, Avinash B.; Mhaske, Pravin C.

doi:10.1002/jhet.2293

Cited by 21 publications

(7 citation statements)

References 36 publications

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“…This protocol (Scheme 2) was further exploited to study its versatility, by subjecting various substituted aromatic aldehydes as well as heteroaromatic aldehyde to give corresponding Isoxazolones in very good yields (Table 2). Characterization studies of prepared compounds revealed parallel similarities with the reported literature data and undoubtedly supported the assigned structures [25–44] …”

Section: Resultssupporting

confidence: 81%

“…Literature analysis [20–44,55–57] revealed this synthetic methodology to be one of the robust method for preparing Isoxazolone derivatives with more labile functional groups. Thus provide scope for development of functionally sensitive or even optically active Isoxazolones, keeping in mind their growing importance in medicinal field.…”

Section: Resultsmentioning

confidence: 99%

“…Characterization studies of prepared compounds revealed parallel similarities with the reported literature data and undoubtedly supported the assigned structures. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] A probable mechanism for this silica supported transformation is given in Scheme 3. The role of silica is herein depicted for activating the dicarbonyl reactant as well as aldehyde and further facilitating the dehydration.…”

Section: Resultsmentioning

confidence: 99%

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Silica Supported Synthesis and Quorum Quenching Ability of Isoxazolones Against Both Gram Positive and Gram Negative Bacterial Pathogens

et al. 2021

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Isoxazolones are synthesised using easily available, economical and reusable silica (TLC grade) catalyst. High yields are obtained in aqueous reaction system with substrate tolerance without affecting the yield. This multigram scale, purification free method exhibits prospects for a large scale use in future. These compounds were screened for their potential application as quorum quenchers in pathogenic bacteria. The prepared compounds were analysed for quorum quenching (QQ) activity on Gram negative bioreporter strain Chromobacterium violaceum by inhibiting its pigment production i. e. violacein production in a concentration dependent manner. Some Isoxazolone derivatives showed very good quorum quenching activity. Moreover these derivatives also showed very good antibiofilm activity against both Gram negative (Pseudomonas aeruginosa ATCC 27853) and Gram positive (Staphylococcus aureus ATCC 6538) bacterial human pathogens through Quorum Quenching mechanism. Isoxazolones thus have enormous potential to be exploited in the medical field against bacterial infections caused by both Gram negative and Gram positive bacterial human pathogens.

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Section: Resultssupporting

confidence: 81%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Silica Supported Synthesis and Quorum Quenching Ability of Isoxazolones Against Both Gram Positive and Gram Negative Bacterial Pathogens

et al. 2021

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“…5). Later Chavan et al (2015) synthesized 4H-isoxazol-5ones efficiently by one-pot uncatalyzed reaction of hydroxylamine hydrochloride, ketoesters and aromatic aldehydes substituted with electron donating group in the aqueous medium. Ji et al (2006)…”

Section: Route Dmentioning

confidence: 99%

The synthetic and therapeutic expedition of isoxazole and its analogs

2018

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Isoxazole, constituting an important family of five-membered heterocycles with one oxygen atom and one nitrogen atom at adjacent positions is of immense importance because of its wide spectrum of biological activities and therapeutic potential. It is, therefore, of prime importance that the development of new synthetic strategies and designing of new isoxazole derivatives should be based on the most recent knowledge emerging from the latest research. This review is an endeavor to highlight the progress in the chemistry and biological activity of isoxazole derivatives which could provide a low-height flying bird's eye view of isoxazole derivatives to the medicinal chemists for the development of clinically viable drugs using this information.

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“…Then, the obtained heterocycles are subjected to further functionalization due to the reactivity of the methylene group as for example in the preparation of arylideneisoxazol‐5‐ones via Knoevenagel condensations , . To this regard, several one‐pot methodologies have been developed, even though the two‐step synthesis remains the most widely used and reliable procedure …”

Section: Introductionmentioning

confidence: 99%

On the Necessity of One‐Pot Tautomer Trapping in Asymmetric Michael Reactions of Arylideneisoxazol‐5‐ones

et al. 2020

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Herein we report the first asymmetric Michael reaction of arylidene-isoxazol-5-one with 1,3-diesters. Despite complex tautomer equilibria of the obtained Michael adducts, the one-pot entrapping strategy by the aid of different electrophiles/ protecting groups led to the selective isolation of diverse N-substituted isoxazol-5-ones in very high overall yield and good enan-Eur.the obtaining of isoindoline based heterocyclic compounds via organocatalytic cascade reactions. [22][23][24][25] Continuing our efforts aiming to develop challenging asymmetric synthesis of complex heterocyclic architectures of isoxazol-5-one, [15] considering the importance to perform sequential reactions in one-pot fashion for atom and step economy, [26] herein we describe the first enantioselective Michael reaction of malonate diesters with arylideneisoxazol-5-ones 1 and the selective tautomer entrapping of the respective adducts with electrophiles. Asymmetric three component Michael/electrophilic tautomer entrapping and four-component Knoevenagel/Michael/electrophilic-tautomer entrapping one-pot protocols have also been investigated and the results have been critically compared.

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An Efficient Synthesis of 4-Arylmethylidene-3-substituted-Isoxazol-5(4H)-ones in Aqueous Medium

Abstract: A series of 4‐arylmethylidene‐3‐substituted‐isoxazol‐5(4H)‐ones were efficiently synthesized by eco‐benign, one pot uncatalyzed reaction of β‐keto‐ester, hydroxylamine hydrochloride, and aromatic aldehyde with electron donating substituent in water.

Cited by 21 publications

References 36 publications

Silica Supported Synthesis and Quorum Quenching Ability of Isoxazolones Against Both Gram Positive and Gram Negative Bacterial Pathogens

Silica Supported Synthesis and Quorum Quenching Ability of Isoxazolones Against Both Gram Positive and Gram Negative Bacterial Pathogens

The synthetic and therapeutic expedition of isoxazole and its analogs

On the Necessity of One‐Pot Tautomer Trapping in Asymmetric Michael Reactions of Arylideneisoxazol‐5‐ones

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