Tetrahedron Letters

Reaction of isatin with alkylating agents with acidic methylenes

MS Shmidt, IA Perillo, M González, MM Blanco

Index: Shmidt, Maria S.; Perillo, Isabel A.; Gonzalez, Mercedes; Blanco, Maria M. Tetrahedron Letters, 2012 , vol. 53, # 20 p. 2514 - 2517

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Citation Number: 17

Abstract

The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solvents leads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads to competitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0–5° C are transformed into the ...