Simple and Efficient Microwave Assisted N-Alkylation of Isatin

doi:10.3390/molecules13040831

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Molecules 2008, 13(4), 831-840; doi:10.3390/molecules13040831

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Simple and Efficient Microwave Assisted N-Alkylation of Isatin

María Sol Shmidt, Ana María Reverdito, Lautaro Kremenchuzky, Isabel Amalia Perillo* and María Mercedes Blanco

Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113) Buenos Aires, República Argentina

* Author to whom correspondence should be addressed.

Received: 11 March 2008; in revised form: 9 April 2008 / Accepted: 9 April 2008 / Published: 10 April 2008

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Abstract: We present herein the results of microwave promoted N-alkylations of isatin (1)with different alkyl, benzyl and functionalized alkyl halides. Reactions were carried outunder different conditions, always employing methodologies compatible with MW assistedchemistry. Generation of isatin anion employing diverse bases and solvents or using thepreformed isatin sodium salt was tested. The best results were achieved using K₂CO₃ orCs₂CO₃ and a few drops of N,N-dimethylformamide or N-methyl-2-pyrrolidinone. Thesereactions present noteworthy advantages over those carried out employing conventionalheating.

Keywords: Isatin; N-alkylation; microwave irradiation; conventional heating; isatin sodium salt

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MDPI and ACS Style

Shmidt, M.S.; Reverdito, A.M.; Kremenchuzky, L.; Perillo, I.A.; Blanco, M.M. Simple and Efficient Microwave Assisted N-Alkylation of Isatin. Molecules 2008, 13, 831-840.

AMA Style

Shmidt MS, Reverdito AM, Kremenchuzky L, Perillo IA, Blanco MM. Simple and Efficient Microwave Assisted N-Alkylation of Isatin. Molecules. 2008; 13(4):831-840.

Chicago/Turabian Style

Shmidt, María S.; Reverdito, Ana M.; Kremenchuzky, Lautaro; Perillo, Isabel A.; Blanco, María M. 2008. "Simple and Efficient Microwave Assisted N-Alkylation of Isatin." Molecules 13, no. 4: 831-840.

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