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2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions

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Chemistry of Heterocyclic Compounds Aims and scope

The N-alkylation of 2- and 3-phenylsulfonylindoles under various conditions and the subsequent removal of the activating phenylsulfonyl group by reductive desulfonylation using Raney nickel leads to N-alkylindoles in high yield. 2-Phenylsulfonylindole readily undergoes the Mitsunobu reaction, while isomeric 3-phenylsulfonylindole is relatively inert under these conditions.

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Authors and Affiliations

  1. Chemistry Faculty, M. V. Lomonosov Moscow State University, Moscow, 119991, Russia

    A. V. Karchava, I. S. Shuleva, A. A. Ovcharenko & M. A. Yurovskaya

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  1. A. V. Karchava
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  2. I. S. Shuleva
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  3. A. A. Ovcharenko
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  4. M. A. Yurovskaya
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Correspondence to A. V. Karchava.

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Dedicated to Professor V. I. Minkin on the occasion of his seventieth birthday.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 373-385, March, 2010.

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Karchava, A.V., Shuleva, I.S., Ovcharenko, A.A. et al. 2- and 3-phenylsulfonylindoles – synthetic equivalents of unsubstituted indole in N-alkylation reactions. Chem Heterocycl Comp 46, 291–301 (2010). https://doi.org/10.1007/s10593-010-0504-3

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  • DOI: https://doi.org/10.1007/s10593-010-0504-3

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