Simple and efficient microwave assisted N-alkylation of isatin.
We present herein the results of microwave promoted N-alkylations of isatin (1)with different alkyl, benzyl and functionalized alkyl halides. Reactions were carried out under different conditions, always employing methodologies compatible with MW assisted chemistry. Generation of isatin anion employing diverse bases and solvents or using the preformed isatin sodium salt was tested. The best results were achieved using K(2)CO(3) or Cs(2)CO(3) and a few drops of N,N-dimethylformamide or N-methyl-2-pyrrolidinone. These reactions present noteworthy advantages over those carried out employing conventional heating.
Shmidt
María Sol
MS
Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956 (1113) Buenos Aires, República Argentina.
Reverdito
Ana María
AM
Kremenchuzky
Lautaro
L
Perillo
Isabel Amalia
IA
Blanco
María Mercedes
MM
D000478:Alkylation; D004852:Epoxy Compounds / Q000138:chemical synthesis; D007510:Isatin / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves
D004852:Epoxy Compounds; D007510:Isatin