The reaction under mild conditions of 1-alkyl-5-hydroxypyrrolidin-2-ones with different indoles having a free 3 position leads exclusively to 1-alkyl-5-(indol-3-yl)pyrrolidin-2-ones but if position 3 is occupied to 1-alkyl-5-(indol-2-yl)pyrrolidin-2-ones.
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Notes
Compound 4c was prepared and introduced in the subsequent reaction as a mixture with the starting imide 7c in the ratio of about 3:2 because both compounds 4c and 7c exist as oils which could not be separated chromatographically. In addition, imide 7c is chemically inert and does not interfere with the subsequent reaction process. The spectroscopic characteristics of compound 4c were obtained and quoted here after subtraction of the spectrum of compound 7c from that of the mixture of compounds produced in the reaction.
For the isomeric 2-(p-tolyl)-1H-indole (9c) in this system R f = 0.75.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1505-1514, October, 2010.
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Sadovoy, A.V., Kovrov, A.E., Golubeva, G.A. et al. Regioselective synthesis of 1-alkyl-5-(indol-3-yl- and -2-yl)pyrrolidin-2-ones from available reagents. Chem Heterocycl Comp 46, 1215–1223 (2011). https://doi.org/10.1007/s10593-011-0655-x
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DOI: https://doi.org/10.1007/s10593-011-0655-x