“On-water” synthesis of thioxoimidazolidinone-isatin/ninhydrin conjugates, followed by temperature-induced dehydration by a ZnMnO<sub>3</sub>@Ni(OH)<sub>2</sub> nano-catalyst

Rana, Soumitra; Basu, Soumyadip; Bera, Aswini; Saha, Pinaki; Ghosh, Prasanta; Khatua, Bhanu Bhusan; Mukhopadhyay, Chhanda

doi:10.1039/d3gc03730d

Cited by 5 publications

(1 citation statement)

References 72 publications

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“…Based on the above results, we have evaluated the green chemistry metrics 23–27 for this reaction on a preparative scale for the synthesis of 3a . The green chemistry metric evaluation for the current green process has an E -factor of 5.70, 93.5% atom economy, 81.1% atom efficiency, 100% carbon efficiency and 67.3% reaction mass efficiency (Table 3).…”

Section: Resultsmentioning

confidence: 99%

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

He,

Li,

Song

et al. 2024

New J. Chem.

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Section: Resultsmentioning

confidence: 99%

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

He,

Li,

Song

et al. 2024

New J. Chem.

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Metal‐Free K₂S₂O₈ Mediated Synthesis of 3‐(Substituted)‐2‐Arylisoindolin‐1‐One Derivatives With Cascade C−N/C−C Bond Formations Via Radical Cyclization

Rana,

Karmakar,

Shee

et al. 2024

Eur J Org Chem

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A facile technique was demonstrated for the synthesis of 2‐hydroxy‐2‐[N‐(alkyl/aryl/heteroaryl)‐3‐oxoisoindolin‐1‐yl]‐1H‐indene‐1,3(2H)‐diones by using a metal‐ free persulfate‐mediated one pot three‐component reaction. The reaction involved the combination effect of TBAB (PTC) and K2S2O8 with the addition of the amine to phthalaldehyde and 2,2‐dihydroxyindane‐1,3‐dione to generate isoindolin‐1‐one in‐situ, followed by cyclization.This lactamization process facilitated the formation of C–N bonds under controllable and ambient reaction conditions. A variety of 2‐hydroxy‐2‐[N‐(substituted)‐3‐oxoisoindolin‐1‐yl]‐1H‐indene‐1,3(2H)‐diones were successfully synthesized through a radical pathway from isoindolin‐1‐one, involving C‐C bond formation. The method demonstrated high functional group compatibility and a wide substrate scope, resulting in moderate to good yields of the desired products. Additionally, the mechanistic analyses demonstrated that isoindolin‐1‐one might be a significant intermediate being involved in the reaction. X‐ray diffraction analysis was used to examine the crystal structures of synthesized 2‐hydroxy‐2‐[N‐(substituted)‐3‐oxoisoindolin‐1‐yl]‐1H‐indene‐1,3(2H)‐diones. Furthermore, it seems that the reaction mechanism involves a radical pathway.

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“In-Water” Three-Component One-Pot Reaction for the Facile Synthesis of Densely Functionalized 2,3-Dihydro-1H-pyrrol-2-ols and Mechanistic Insight

Saigal,

Sudheer,

Sahoo

et al. 2024

ACS Sustainable Chem. Eng.

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An environmentally friendly multicomponent reaction strategy for the synthesis of functionally rich all-carbon substituted 2,3-dihydro-1H-pyrrol-2-ols "in-water" at room temperature has been reported. Water plays an indispensable role in the presence of readily available catalytic surfactants sodium dioctylsulfosuccinate and sodium dodecyl sulfate to effectuate the transformation, as has been proved by inferior results obtained in organic solvents. A wide display of substrate scope and functional group compatibility permits diversity generation in a mild operationally simple fashion. High product yields, fast reaction rate, recoverability/recyclability of the catalysts, high TON/TOF, ease of purification of final products by filtration, high AE values, and excellent E-factor count with the score as low as possible highlight the "greenness" of this approach. Feasibility of "gram-scale" synthesis and synthetic elaboration of the final product offer notable advantages. The mechanistic understanding by intercepting labile "imine" intermediate has been realized through a sequence of imine formation and Mannich-type reaction followed by intramolecular N-cyclization.

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“On-water” synthesis of thioxoimidazolidinone-isatin/ninhydrin conjugates, followed by temperature-induced dehydration by a ZnMnO₃@Ni(OH)₂ nano-catalyst

Cited by 5 publications

References 72 publications

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

Metal‐Free K₂S₂O₈ Mediated Synthesis of 3‐(Substituted)‐2‐Arylisoindolin‐1‐One Derivatives With Cascade C−N/C−C Bond Formations Via Radical Cyclization

“In-Water” Three-Component One-Pot Reaction for the Facile Synthesis of Densely Functionalized 2,3-Dihydro-1H-pyrrol-2-ols and Mechanistic Insight

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“On-water” synthesis of thioxoimidazolidinone-isatin/ninhydrin conjugates, followed by temperature-induced dehydration by a ZnMnO3@Ni(OH)2 nano-catalyst

Cited by 5 publications

References 72 publications

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

Efficient synthesis of bioactive isoindolinone derivatives containing continuous quaternary carbons by intermolecular OH transfer

Metal‐Free K2S2O8 Mediated Synthesis of 3‐(Substituted)‐2‐Arylisoindolin‐1‐One Derivatives With Cascade C−N/C−C Bond Formations Via Radical Cyclization

“In-Water” Three-Component One-Pot Reaction for the Facile Synthesis of Densely Functionalized 2,3-Dihydro-1H-pyrrol-2-ols and Mechanistic Insight

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“On-water” synthesis of thioxoimidazolidinone-isatin/ninhydrin conjugates, followed by temperature-induced dehydration by a ZnMnO₃@Ni(OH)₂ nano-catalyst

Metal‐Free K₂S₂O₈ Mediated Synthesis of 3‐(Substituted)‐2‐Arylisoindolin‐1‐One Derivatives With Cascade C−N/C−C Bond Formations Via Radical Cyclization