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Synthesis of 1- and 2-Carbamoylalkyl-2,3-dihydro-1H-indole and 9-Carbamoylalkyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole Derivatives

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Abstract

Treatment of 1,2,3,9a-tetrahydro-9H-imidazo- and 1,2,3,4,10,10a-hexahydropyrimido[1,2-a]indol-2-one derivatives with formic acid gave 1-carbamoylalkyl-2,3,3-trimethyl-2,3-dihydro-1H-indoles. 9-Carbamoylmethyl- and 9-(2-carbamoylethyl)-4a-methyl-2,3,4,4a,9,9a-hexahydro-1H-carbazoles were prepared from 5,6,7,7a-tetrahydro-1H,4H-imidazo- and 1,2,6,7,8,8a-hexahydro-5H-pyrimido[2,1-k]carbazolones in a similar manner. Synthesis of 2-(2-carbamoylpropyl)-2,3,3-trimethyl-2,3-dihydro-1H-indole was carried out by reduction of 1,3-dihydrospiro[2H-indolo-2,2'-piperidine] derivative with Zn in acetic acid solution.

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Authors and Affiliations

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

    V. Amankaviciene, S. Krikstolaityte & A. Sackus

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  1. V. Amankaviciene
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  2. S. Krikstolaityte
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  3. A. Sackus
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Amankaviciene, V., Krikstolaityte, S. & Sackus, A. Synthesis of 1- and 2-Carbamoylalkyl-2,3-dihydro-1H-indole and 9-Carbamoylalkyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole Derivatives. Chemistry of Heterocyclic Compounds 38, 686–691 (2002). https://doi.org/10.1023/A:1019965202484

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  • DOI: https://doi.org/10.1023/A:1019965202484

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