Water-acetic acid mediated an efficient and eco-friendly protocol for the one-pot synthesis of bis-isoxazolyl amino dihydro-1 H -indol-4(5 H )-ones under mild reaction conditions

Reddy, M. Nagi; Kumar, Pittala Praveen

doi:10.1016/j.tetlet.2017.11.027

Cited by 11 publications

(4 citation statements)

References 53 publications

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“…The generality of the reaction was established by employing Nisoxazolyl enaminone 76 with arylglyoxals 4 and a series of isoxazoles 75, 77, and 79 in the reaction process to produce the desired products in good to excellent yields in water and AcOH as catalyst under metal-free and refluxing conditions (Scheme 29). 101 Scheme 29. The synthesis of bis-isoxazolyl-1H-indol-4(5H)-one derivatives of Reddy and Kumar.…”

Section: Synthesis Of 1567-dihydro-4h-indol-4-ones and Other Indolesmentioning

confidence: 99%

“…The synthesis of bis-isoxazolyl-1H-indol-4(5H)-one derivatives of Reddy and Kumar. 101 Maity's group has reported the simple reaction of arylglyoxals 4 and enaminones 63, for the synthesis of fused pyrrole derivatives 81 through microwave-assisted reactions under neutral conditions and in a nonnucleophilic solvent, without the use of any catalyst (Scheme 30). 102 Scheme 30.…”

Section: Synthesis Of 1567-dihydro-4h-indol-4-ones and Other Indolesmentioning

confidence: 99%

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Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

Javahershenas¹,

Arlan²,

Prager³

et al. 2020

Arkivoc

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Pyrrole is widely known as an active pharmacophore. This core framework plays an important role in several natural and biological products. Due to its properties, developing such scaffolds has attracted much attention. The accessibility of these role-playing heterocyclic motifs via easy, high efficiency and developed methodologies is of interest and value in the creation of new heterocyclic compounds. This review highlights the broad range of applications of arylglyoxals in the synthesis of pyrrole derivatives via multicomponent reactions over the period 2010-2019.

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Section: Synthesis Of 1567-dihydro-4h-indol-4-ones and Other Indolesmentioning

confidence: 99%

Section: Synthesis Of 1567-dihydro-4h-indol-4-ones and Other Indolesmentioning

confidence: 99%

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

Javahershenas¹,

Arlan²,

Prager³

et al. 2020

Arkivoc

View full text Add to dashboard Cite

show abstract

“…In the synthesis of biologically active functional compounds, development of inexpensive and environmentally friendly protocols is highly desirable [21] . Looking at various new methods used for the synthesis of isoxazoline compounds, it appears that most of these methods utilize transition metals, [22] or involve multi‐step processes, which are unfavorable for their scale‐up.…”

Section: Introductionmentioning

confidence: 99%

“…In the synthesis of biologically active functional compounds, development of inexpensive and environmentally friendly protocols is highly desirable. [21] Looking at various new methods used for the synthesis of isoxazoline compounds, it appears that most of these methods utilize transition metals, [22] or involve multistep processes, which are unfavorable for their scaleup. Moreover, they face challenges due to the high cost and toxicity of the catalysts involved, as well as owing to the difficulties encountered in purifying the products and disposing off the waste and by-products generated in the reaction process.…”

Section: Introductionmentioning

confidence: 99%

N‐Chlorosuccinimide‐Promoted One‐Pot Synthesis of Substituted 4,5‐Dihydroisoxazole‐5‐methanols in Aqueous Medium

Jia

Ablajan

2023

Adv Synth Catal

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Herein, a catalyst‐free method for synthesizing 4,5‐dihydroisoxazole‐5‐methanols is proposed, whereby isoxazolines are constructed through the NCS‐mediated 1,3‐dipolar cycloaddition reaction of aldoximes and allyl alcohol in the presence of K2CO3 at room temperature via a one‐pot route. The reaction was achieved in water medium to introduce a low‐cost direct protocol for synthesizing isoxazolines. This method offers advantages including the use of an oxidant‐free and transition metal‐free approach, broad scope of allyl alcohol and aldoxime substrates, room‐temperature reaction, good to higher yields (42–92%), and involvement of a gram‐scale synthesis.

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Efficient Construction of 5H‐1,4‐Benzodiazepine Derivatives by a Catalyst‐Free Direct Aerobic Oxidative Annulation Strategy

et al. 2021

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A catalyst‐free direct aerobic oxidative annulation reaction of 2‐aminobenzylic amines and α‐hydroxy ketones efficiently afforded versatile 5H‐1,4‐benzodiazepine derivatives by employing air as economic and green oxidant under mild conditions. Interestingly, solvent was found to be crucial to the reaction, so that by using acetic acid as the best solvent an efficient and practical method could be achieved, requiring no catalysts or additives at all. This method tolerates a wide range of 2‐aminobenzylic amines and α‐hydroxy ketones and could be scaled up to multigram synthesis and directly applied in one‐step synthesis of the pharmaceutically active N‐desmethylmedazepam derivatives, revealing the potential of this new method in the synthesis of 5H‐1,4‐benzodiazepine skeleton‐based pharmaceuticals and chemicals.

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Water-acetic acid mediated an efficient and eco-friendly protocol for the one-pot synthesis of bis-isoxazolyl amino dihydro-1 H -indol-4(5 H )-ones under mild reaction conditions

Cited by 11 publications

References 53 publications

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

Recent advances in the synthesis of pyrroles via multicomponent reactions using arylglyoxals

N‐Chlorosuccinimide‐Promoted One‐Pot Synthesis of Substituted 4,5‐Dihydroisoxazole‐5‐methanols in Aqueous Medium

Efficient Construction of 5H‐1,4‐Benzodiazepine Derivatives by a Catalyst‐Free Direct Aerobic Oxidative Annulation Strategy

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