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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 14
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Original Articles

Rapid and Efficient Synthesis of 3,3-Di(1H-indol-3-yl)indolin-2-ones and 2,2-Di(1H-indol-3-yl)-2H-acenaphthen-1-ones Catalyzed by p-TSA

, , , &
Pages 2029-2036 | Received 19 Aug 2013, Published online: 09 Jun 2014
 

Abstract

An efficient synthesis of 3,3-di(1H-indol-3-yl)indolin-2-ones and 2,2-di(1H-indol-3-yl)-2H-acenaphthen-1-ones via a reaction of various isatins or acenaphthenequinone with indoles in the presence of p-methylbenzene sulfonic acid (p-TSA) in CH2Cl2 at room temperature is described. The advantages of this method include good reaction yield, simple workup procedure, and mild reaction condition.

GRAPHICAL ABSTRACT

Notes

a Reaction conditions: isatin 1a (1 mmol), indole 2a (2 mmol), solvent (5 mL).

b r.t. = room temperature.

c Isolated yields.

a Reaction conditions: isatin 1 (1 mmol), indole 2 (2 mmol), p-TSA (10 mol %), CH2Cl2 (5 mL), rt.

b Isolated yields.

c, d, e, f Yields of reported literature.[ Citation 26 , Citation 13 , Citation 16 , Citation 27 ]

a Reaction conditions: acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10 mol %), CH2Cl2 (5 mL), rt.

b Isolated yields.

c Yields of reported literature.[ Citation 31 ]

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