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Alkylation of 1,2,3,4,10,10a-hexahydropyrimido[1,2-a]indol-2-one

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A mixture of N- and O-alkylation products is formed in the reaction of 1,2,3,4,10,-10a-hexahydropyrimido[1,2-a]indol-2-ones with ethyl iodide, allyl bromide, or benzyl chloride in DMFA (dimethylformamide) in the presence of potassium hydroxide. In the presence of aqueous solutions of acids with subsequent treatment with bases, the alkylation products are converted to 1-[2-(alkoxycarbonyl)-ethyl]-2-methylene-2,3-dehydro-1H-indoles. The reaction of 1,2,3,4,10,10a-hexahydropyrimido[1,2-a]indol-2-one with triethyloxonium fluoroborate gives 1-[2-(ethoxycarbonyl)ethyl]-2-methylene-2,3-dihydro-1H-indole.

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Authors and Affiliations

  1. A. Snechkus Kaunas Polytechnic Institute, 233006, Kaunas

    R. Yu. Dyagutite & A. A. Shachkus

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  1. R. Yu. Dyagutite
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  2. A. A. Shachkus
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1224–1227, September, 1989.

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Dyagutite, R.Y., Shachkus, A.A. Alkylation of 1,2,3,4,10,10a-hexahydropyrimido[1,2-a]indol-2-one. Chem Heterocycl Compd 25, 1024–1027 (1989). https://doi.org/10.1007/BF00487302

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  • DOI: https://doi.org/10.1007/BF00487302

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