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Synthesis of 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9h-imidazo[1,2-a]-indol-2-ones by reaction of 2,3,3-trimethyl-3h-indole with 2-bromopropionamides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Alkylation of 2,3,3-trimethyl-3H-indole with 2-bromopropionamide and the subsequent treatment of the formed 1-(1-carbamoylethyl)-2,3,3-trimethyl-3H-indolium bromide with a base afforded 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one. Condensation of the 1-(1-carbamoylethyl)-2,3,3-trimethyl-3H-indolium salt with 2-hydroxy-1-naphthaldehyde gave a mixture of diastereomeric 1-(1-carbamoylethyl)spiro[2H-indole-2,3’-[3H]naphtho[2,1-b]pyrans].

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Authors and Affiliations

  1. Department of Organic Chemistry, Kaunas University of Technology, LT-3028, Kaunas, Lithuania

    E. Valaityte, V. Martynaitis & A. Sackus

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  1. E. Valaityte
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  2. V. Martynaitis
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  3. A. Sackus
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Published in Khimiya Geterotsiklicheskikh Soedinenii, No 11, pp. 1690–1694, November, 2004.

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Valaityte, E., Martynaitis, V. & Sackus, A. Synthesis of 3,9,9,9a-tetramethyl-1,2,3,9a-tetrahydro-9h-imidazo[1,2-a]-indol-2-ones by reaction of 2,3,3-trimethyl-3h-indole with 2-bromopropionamides. Chem Heterocycl Compd 40, 1460–1464 (2004). https://doi.org/10.1007/PL00021792

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  • DOI: https://doi.org/10.1007/PL00021792

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