Simple and Efficient Method for the Synthesis of 1-((Aryl)(2-oxoindolin-3-yl-)methyl)urea and 1-((Aryl)(2-oxoindolin-3-yl-)methyl)thiourea Derivatives

Abstract

A number of new1-((aryl)(2-oxoindolin-3-yl)methyl)urea and 1-((aryl)(2-oxoindolin-3-yl)methyl)thiourea derivatives have been prepared by simply combining 2-indolinone, aromatic aldehyde, and urea or thiourea in the presence of p-TsOH in EtOH. This new methodology affords the title compounds in good yields and without the use of chromatography.

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GRAPHICAL ABSTRACT

Keywords:

• Green chemistry
• 2-indolinone
• multicomponent reaction
• p-TsOH

ACKNOWLEDGMENTS

This work was supported by the Chinese National Science and Technology Major Project Key New Drug Creation and Manufacturing Program (Grants 2009ZX09301-001 and 2009ZX09102-022) and the National Natural Science Foundation of China (Grants 30925040, 81102329, and 90713046).

Notes

^a Conditions: 2-indolinone 1 (2 mmol), benzaldehyde 2a (2 mmol), urea 3a (3 mmol), and solvent (2 mL).

^b Isolated yields.

^a Conditions: 2-indolinone 1 (2 mmol), aromatic aldehyde 2 (2 mmol), urea 3a (3 mmol) or thiourea 3b (3 mmol), p-TsOH (0.3 mmol, 15 mol %), EtOH (2 mL), reflux temperature.

^b Isolated yields.

^c Only product 5 was observed.