Cu(OAc)2 catalyzed ultrasound assisted rapid synthesis of isocoumarin derivatives bearing 3-oxobutyl moiety at C-4 position

Ramarao, Sidda; Pothireddy, Mohanreddy; Venkateshwarlu, Rapolu; Moturu, Krishna Murthy V. R.; Siddaiah, Vidavalur; Dandela, Rambabu; Pal, Manojit

doi:10.1016/j.molstruc.2022.132418

Cited by 6 publications

(4 citation statements)

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“…The reaction was performed under a range of conditions (Table 1). Based on our previous success, [28] Cu(OAc) 2 (10 mol%) was chosen as the catalyst initially. The reaction did not proceed when carried out at 80 °C for 6 h in the absence of any base (entry 1, Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…[25,26] Several metal catalyzed reactions have been reported to be accelerated by ultrasound irradiation that was thought to be because of synergy between catalysis and ultrasound, implosion of cavitation bubbles on the catalytic surface thereby activating the catalyst etc. [26] Due to our interest in this area [27,28] herein, we report ultrasound assisted αarylation of ketones (2) using 2-iodobenzamide (1) as the aryl halide in the presence of CuI affording a rapid and greener access to various isoquinolin-1(2H)-one derivatives (3, Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

et al. 2022

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In the current study we have demonstrated the effectiveness of ultrasound, a source of green energy, in accessing various isoquinolin‐1(2H)‐one derivatives via the sequential two‐step reaction in a single pot. The methodology involved ultrasound assisted Cu‐catalyzed α‐arylation of ketones with 2‐iodobenzamide (via a C−C bond formation) followed by intramolecular cyclization (via the C−N bond formation) in the same pot. The role of ultrasound, catalyst, base and solvent in the current transformation was evaluated and the generality as well as scope of the methodology was examined via synthesizing a variety of compounds in acceptable to good (49–93 %) yields. The application potential of the methodology was demonstrated further via synthesizing a reported bioactive arylisoquinolinamine derivative of medicinal significance. Further, the encouraging inhibition of TNF‐α in vitro (>50 % at 10 μM) was shown by some of the synthesized compounds e. g. 3 j, 3 m and 3 p.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

et al. 2022

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“…During the past three decades, sonochemistry has been considered as an effective procedure for synthesis of numerous organic compounds. [1][2][3][4][5][6] The preparation of organic compounds under ultrasound conditions often needs fewer solvents and catalysts, which means an environment-friendly and green method. In other words, the green chemistry purposes such as decrease of energy necessities and waste minimization can be obtained with ultrasound-assisted reactions.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, the application of ultrasound waves can be exceedingly advantageous. During the past three decades, sonochemistry has been considered as an effective procedure for synthesis of numerous organic compounds [1–6] . The preparation of organic compounds under ultrasound conditions often needs fewer solvents and catalysts, which means an environment‐friendly and green method.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound Probe‐assisted Telescopic One‐pot Synthesis of Spiro[indene‐2,2’‐naphthalene]‐4’‐carbonitrile Derivatives using Fe₃O₄@SCH₂CO₂H@Ni‐NH₂as a Reusable Nanocatalyst

2023

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In this paper, a novel inorganic‐organic hybrid catalyst based on Fe3O4 has been successfully developed during four simple steps. After construction of Fe3O4@SCH2CO2H, the presence of nickel and urea converts this catalyst into the porous nano magnetic catalyst. The prepared nanocatalyst was identified by FT‐IR, VSM, XRD, FE‐SEM, EDX, elemental mapping, TGA, TEM, and BET. Then, we have employed the prepared catalyst as a recoverable heterogeneous and nanoporous catalyst for synthesis of spiro[indene‐2,2’‐naphthalene]‐4’‐ carbonitrile derivatives via one‐pot telescopic four component reaction of malononitrile, cyclohexanone, aromatic aldehydes, and 1,3‐indandione under ultrasonic irradiation. As anticipated, prepared catalyst displayed significant performance in the promoting of the studied reaction. Eco‐friendly, facile workup, medium to excellent yields in short reaction times, broad range of products, high catalytic performance and reusability of the catalyst are some of the noticeable advantages of this protocol. Further, we can separate and reuse the catalyst six times without any significant loss of activity.

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Sonochemical synthesis, docking studies and in vitro evaluation of imidazo-1,3-oxazinone derivatives as potential inhibitors of TNF-α

Rao,

Taneja,

Tej

et al. 2023

Journal of Molecular Structure

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Cu(OAc)2 catalyzed ultrasound assisted rapid synthesis of isocoumarin derivatives bearing 3-oxobutyl moiety at C-4 position

Cited by 6 publications

References 37 publications

Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

Ultrasound Probe‐assisted Telescopic One‐pot Synthesis of Spiro[indene‐2,2’‐naphthalene]‐4’‐carbonitrile Derivatives using Fe₃O₄@SCH₂CO₂H@Ni‐NH₂as a Reusable Nanocatalyst

Sonochemical synthesis, docking studies and in vitro evaluation of imidazo-1,3-oxazinone derivatives as potential inhibitors of TNF-α

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Cu(OAc)2 catalyzed ultrasound assisted rapid synthesis of isocoumarin derivatives bearing 3-oxobutyl moiety at C-4 position

Cited by 6 publications

References 37 publications

Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

Ultrasound Assisted α‐Arylation of Ketones: A Rapid Access to Isoquinolinone Derivatives

Ultrasound Probe‐assisted Telescopic One‐pot Synthesis of Spiro[indene‐2,2’‐naphthalene]‐4’‐carbonitrile Derivatives using Fe3O4@SCH2CO2H@Ni‐NH2as a Reusable Nanocatalyst

Sonochemical synthesis, docking studies and in vitro evaluation of imidazo-1,3-oxazinone derivatives as potential inhibitors of TNF-α

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Ultrasound Probe‐assisted Telescopic One‐pot Synthesis of Spiro[indene‐2,2’‐naphthalene]‐4’‐carbonitrile Derivatives using Fe₃O₄@SCH₂CO₂H@Ni‐NH₂as a Reusable Nanocatalyst