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Indole derivatives. 138. Synthesis of α-(5-indolyl)ethylamine and 5-(2-aminoethoxy)- and 5-(aminoethylthio)tryptamines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 5-acetylindole with hydroxylamine with subsequent reduction of the resulting oxime gave α-(5-indolyl)ethylamine. Coupling of 4-(2-phthalimidoethoxy)- and 4-(2-phthalimidoethylthio)phenyldiazonium chlorides with ethyl α-acetyl-δ-phthalimidovalerate, subsequent cyclization of the resulting hydrazones, hydrolysis, decarboxylation, and removal of the phthalyl protecting group led to the formation of 5-(2-aminoethoxy)- and 5-(2-aminoethylthio)tryptamines, respectively.

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Authors and Affiliations

  1. D. I. Mendeleev Chemical and Technological Institute, Moscow

    E. N. Gordeev, V. N. Buyanov & V. E. Zhigachev

Authors
  1. E. N. Gordeev
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  2. V. N. Buyanov
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  3. V. E. Zhigachev
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Additional information

For Communication 137, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 46–48, January, 1992.

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Gordeev, E.N., Buyanov, V.N. & Zhigachev, V.E. Indole derivatives. 138. Synthesis of α-(5-indolyl)ethylamine and 5-(2-aminoethoxy)- and 5-(aminoethylthio)tryptamines. Chem Heterocycl Compd 28, 40–42 (1992). https://doi.org/10.1007/BF00529476

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  • DOI: https://doi.org/10.1007/BF00529476

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