A simple and eco-friendly synthesis of 3-indolyl-3-hydroxy oxindoles and 11-indolyl-11H-indeno[1,2-b]quinoxalin-11-ols in aqueous media

Shanthi, Gnanamani; Lakshmi, Neelakandan Vidhya; Perumal, Paramasivan T.

doi:10.3998/ark.5550190.0010.a12

Cited by 29 publications

(1 citation statement)

References 7 publications

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“…In the case of 3-indolyl-3-hydroxy oxindoles, Kumar and co-workers reported the synthesis of various 3-indolyl-3-hydroxy oxindoles by supramolecular catalysis (β-Cyclodextrin) in 45 -190 minutes [7]; Shanthi and co-workers reported a time of 60 -120 minutes using K 2 CO 3 as a catalyst [26]; Meshram and co-workers reported a time of 15 minutes in the presence of Triton B [27]; Hosseini and Tavakolian reported a reaction time of 2.5 h using ZnO nanorods in aqueous medium [28]. EtOH and water medium (60:40) in the presence of Lewis acid (FeCl 3 •6H 2 O) and ultrasonic irradiation in 5 -25 minutes was reported by Khorshidi and Tabatabaeian [29] while Makarem and co-workers reported an electrochemical method using EtOH/Propanol (60 -240 minutes) [30].…”

Section: Introductionmentioning

confidence: 99%

Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones

Vuram¹,

Kabilan²,

Chadha³

2015

IJOC

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A simple and efficient method for the synthesis of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2-ones using microwave irradiation without catalyst and solvent is described. A series of 3-indolyl-3-hydroxy oxindoles and unsymmetrical 3,3-di(indolyl)indolin-2ones have been synthesized in very short reaction times of 5 and 10 minutes and in yields ranging from 31% to 98% and from 53% to 78% respectively. This method offers a significant advantage over the conventional methods in terms of simplicity and shorter reaction time. To the best of our knowledge compounds N-allyl-3-hydroxy-3-(1-methyl-indol-3-yl)indolin-2-one (6c), N-allyl-3hydroxy-3-(5-methoxy-indol-3-yl)indolin-2-one (8c), N-benzyl-3-hydroxy-3-(1-methyl-indol-3-yl) indolin-2-one (10c), N-propargyl-3-hydroxy-3-(1-methyl-indol-3-yl)indolin-2-one (13c), N-propargyl-3-hydroxy-3-(5-methoxy-indol-3-yl)indolin-2-one (14c), 3-(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (1e), 3-1-methyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (2e), 3-1-allyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (3e), 3-1-benzyl(5-methoxy-1H-indol-3-yl)-3-(1H-indol-3-yl)indolin-2-one (4e) and 3-1-(prop-2-ynyl)(5-methoxy-1H-indol-3-yl)-3(1Hindol-3-yl)indolin-2-one (5e) are reported here for the first time. All the compounds are characterized by IR, 1 H, 13 C NMR and HRMS.

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Section: Introductionmentioning

confidence: 99%

Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones

Vuram¹,

Kabilan²,

Chadha³

2015

IJOC

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Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine

et al. 2011

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Konstruktiver Beitrag: Die Titelreaktion unter Beteiligung von 3‐Hydroxyoxindolen liefert Oxindole mit einem rein C‐substituierten quartären stereogenen Zentrum in hoher Ausbeute und mit exzellenter Enantioselektivität. Die Reaktion ermöglichte die enantioselektive Synthese von Hexahydropyrroloindol‐Gerüsten und die erste katalytische enantioselektive Totalsynthese von (+)‐Folicanthin.

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Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine

et al. 2011

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A simple and eco-friendly synthesis of 3-indolyl-3-hydroxy oxindoles and 11-indolyl-11H-indeno[1,2-b]quinoxalin-11-ols in aqueous media

Abstract: A simple and convenient method for the synthesis of 3-indolyl-3-hydroxy oxindoles and 11-indolyl-11H-indeno[1,2-b]quinoxalin-11-ols catalyzed by K 2 CO 3 in aqueous media is described.

Cited by 29 publications

References 7 publications

Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones

Catalyst and Solvent-Free Microwave Assisted Expeditious Synthesis of 3-Indolyl-3-hydroxy Oxindoles and Unsymmetrical 3,3-Di(indolyl)indolin-2-ones

Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine

Core‐Structure‐Oriented Asymmetric Organocatalytic Substitution of 3‐Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)‐Folicanthine

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