The reduction of activated 5-(indol-3-yl)pyrrolidin-2-ones leading to a mixture of the respective indolyl pyrrolidines and their borane complexes, as well as several other transformations indicate that the electrophilicity of carbonyl group in 5-indolylpyrrolidin-2-ones is significantly decreased.
Similar content being viewed by others
Notes
Here and below М(base) – the molar mass of the base.
References
Kharkevich, D. F. Pharmacology [in Russian]; GEOTAR Meditsina: Moscow, 2000, p. 62, 496.
Granik, V. G. Fundamentals of Medicinal Chemistry [in Russian]; Vuzovskaya Kniga: Moscow, 2006, p. 68, 259, 270.
Kovalenko, L. V. Biochemical Foundations of the Chemistry of Biologically Active Compounds [in Russian]; BINOM: Moscow, 2010, p. 73, 77.
Sadovoy, A. V.; Kovrov, A. E.; Golubeva, G. A.; Sviridova, L. A. Chem. Heterocycl. Compd. 2011, 46, 1215. [Khim. Geterotsikl. Soedin. 2010, 1505.]
Granik, V. G. Acetals of Amides and Lactams [in Russian]; Vuzovskaya Kniga: Moscow, 2008, p. 9, 149.
Shu, C.; Liu, M.-Q.; Wang, S.-S.; Li, L.; Ye, L.-W. J. Org. Chem. 2013, 78, 3292.
Kuehne, M. E.; Shannon, P. J. J. Org. Chem. 1977, 42, 2082.
Atta-ur-Rahman; Basha, A.; Waheed, N.; Ahmed S. Tetrahedron Lett. 1976, 17, 219.
X-AREA and X-RED32. STOE & Cie GmbH: Darmstadt, 2012.
Walker, N.; Stuart, D. Acta Crystallogr., Sect. A: Found. Crystallogr. 1983, A39, 158.
Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.
Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(1), 21–24
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(PDF 266 kb)
Rights and permissions
About this article
Cite this article
Sadovoy, A.V., Nikitina, V.N., Rybakov, V.B. et al. Reduction of 5-(indol-3-yl)pyrrolidin-2-ones. Chem Heterocycl Comp 52, 21–24 (2016). https://doi.org/10.1007/s10593-016-1832-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-016-1832-8