Phase transfer catalyzed synthesis of 3‐methyl‐4<i>h</i>‐pyrazolo[3,4‐<i>d</i>]isoxazole from 3,5‐dimethyl‐4‐isoxazolyldiazonium tetrafluoroborate

Rajanarendar, E.; Mohan, G. Krishna; Ramesh, P.; Srinivas, M.

doi:10.1002/jhet.5570440134

Cited by 16 publications

(2 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Based on the significance of pharmacological profile of isoxazole derivatives, and as a sequel to our work on the synthesis of biologically important isoxazolyl heterocycles with potent anticancer activity, we herein, describe the green route for synthesis of novel isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1 H ‐3‐indolyl)pyrrole‐3‐carboxylates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Anti‐inflammatory Activity of Novel Isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1H‐3‐indolyl)pyrrole‐3‐carboxylates

Saini

Nagaraju

Rajanarendar

et al. 2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A series of novel isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1H‐3‐indolyl)pyrrole‐3‐carboxylates (17a–i) were synthesized by a three‐component reaction of 4‐amino‐3‐methyl‐5‐styrylisoxazole 14, β‐keto ester 15, and 3‐phenacylideneoxindole 16, in the presence of CAN catalyst in ethanol. The structures of the synthesized compounds have been established on the basis of spectral and analytical data. The title compounds 17a–i were evaluated for their anti‐inflammatory activity. Compounds 17b and 17c exhibited potent anti‐inflammatory activity as that of standard drug.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Anti‐inflammatory Activity of Novel Isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1H‐3‐indolyl)pyrrole‐3‐carboxylates

Saini

Nagaraju

Rajanarendar

et al. 2017

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…[10][11][12] Similarly, 1-methyl imidazolium tetrafluoroborates has been exploited as an efficient Bronsted acid promoter ionic liquid in various organic transformations. [13][14][15] As a part of our study on environmentally friendly organic synthesis with isoxazoles, [16][17][18][19] avoiding organic solvent and toxic catalyst in reactions, we demonstrated the use of room temperature ionic liquids as efficient catalysts as well as reaction media for Knoevenagel and Michael reactions and also for conducting reductive cyclization.Looking for a valuable procedure for the conversion of nitro styrylisoxazoles (3) to pyrrolo[2,3-d]isoxazoles (4), several approaches have been investigated. One method for pyrrole ring formation is by de-oxygenative cyclization of nitro styryl compounds using triethyl phosphite (TEP).…”

mentioning

confidence: 99%

A Fast and Highly Efficient Protocol for Synthesis of Pyrrolo[2,3-d]isoxazoles and a New Series of Novel Benzyl Bis-pyrrolo[2,3-d]isoxazoles Using Task-Specific Ionic Liquids as Catalyst and Green Solvent

et al. 2010

View full text Add to dashboard Cite

Regular ArticleSignificant progress in green chemistry is being made in several key research areas, such as catalysis, 1) the design of safer chemicals, environmentally benign solvents 2) and the development of renewable feed stocks. Chemists are trained to design products and processes with an increased awareness of environmental impact. Outreach activities within the green chemistry community highlight the potential for chemistry to solve many of the global environmental challenges. In the recent years, ionic liquids have emerged as green solvents with desirable properties such as good solvating ability, wide liquidous range, tunable polarity, high thermal stability, negligible vapour pressure and ease of recyclability. These are referred to as designer solvents since they exhibit properties like hydrophilicity, hydrophobicity, Lewis acidity, viscosity and density. These can be altered by the fine tuning of parameters such as the choice of organic cation and the length of alkyl chain attached to an organic cation. These structural variations offer flexibility to the chemists to devise the most idealized solvent catering to the needs of any particular process. Due to the stabilization of charged intermediates by ionic liquids, they can promote unprecedented selectivities and enhanced reaction rates. Consequently, ionic liquids are being used as recyclable solvents for the immobilization of transition metal-based catalysts, Lewis acids and enzymes. During the past few years, a variety of room temperature ionic liquids have been demonstrated as efficient and practical alternatives to organic solvents for many important organic transformations. [3][4][5][6][7][8][9] Particularly, the use of [bmIm]OH as a novel and a recyclable reaction medium, as well as an efficient catalyst for Knoevenagel and Michael reactions has been reported in literature. [10][11][12] Similarly, 1-methyl imidazolium tetrafluoroborates has been exploited as an efficient Bronsted acid promoter ionic liquid in various organic transformations. [13][14][15] As a part of our study on environmentally friendly organic synthesis with isoxazoles, [16][17][18][19] avoiding organic solvent and toxic catalyst in reactions, we demonstrated the use of room temperature ionic liquids as efficient catalysts as well as reaction media for Knoevenagel and Michael reactions and also for conducting reductive cyclization.Looking for a valuable procedure for the conversion of nitro styrylisoxazoles (3) to pyrrolo[2,3-d]isoxazoles (4), several approaches have been investigated. One method for pyrrole ring formation is by de-oxygenative cyclization of nitro styryl compounds using triethyl phosphite (TEP). [20][21][22] As the reaction requires heating of the nitro styrylisoxazole (3) in TEP at high temperature under N 2 atmosphere, the reaction results in cleavage of the isoxazole ring, which is unstable at higher temperature. 23) To overcome this problem, another method developed by Angelo Carotti 24) is employed, which involves the reductive cyclization of a nitro s...

show abstract

Phase Transfer Catalyzed Synthesis of 3‐Methyl‐4H‐pyrazolo[3,4‐d]isoxazole from 3,5‐Dimethyl‐4‐isoxazolyldiazonium Tetrafluoroborate.

et al. 2007

Self Cite

View full text Add to dashboard Cite

show abstract

Phase transfer catalyzed synthesis of 3‐methyl‐4h‐pyrazolo[3,4‐d]isoxazole from 3,5‐dimethyl‐4‐isoxazolyldiazonium tetrafluoroborate

Cited by 16 publications

References 8 publications

Synthesis, Characterization, and Anti‐inflammatory Activity of Novel Isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1H‐3‐indolyl)pyrrole‐3‐carboxylates

Synthesis, Characterization, and Anti‐inflammatory Activity of Novel Isoxazolyl‐4‐(2‐oxo‐2,3‐dihydro‐1H‐3‐indolyl)pyrrole‐3‐carboxylates

A Fast and Highly Efficient Protocol for Synthesis of Pyrrolo[2,3-d]isoxazoles and a New Series of Novel Benzyl Bis-pyrrolo[2,3-d]isoxazoles Using Task-Specific Ionic Liquids as Catalyst and Green Solvent

Phase Transfer Catalyzed Synthesis of 3‐Methyl‐4H‐pyrazolo[3,4‐d]isoxazole from 3,5‐Dimethyl‐4‐isoxazolyldiazonium Tetrafluoroborate.

Contact Info

Product

Resources

About