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Condensation of 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolium chloride with aromatic aldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolium chloride with various aromatic aldehydes in acetic acid and the subsequent workup of the intermediate styrylic derivatives with strong bases yielded 9a-(2-arylethenyl)-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one derivatives. Condensation of the mentioned salt with salicylaldehyde in acidic or basic medium afforded the derivative of l′-carbamoylmethylspiro[benzopyran-2,2′-indole]. Alkylation of the latter compound with benzyl chloride in the presence of potassium hydroxide gave 9a-[2-(2-benzyloxyphenyl)ethenyl]-1,2,3,9a-tetrahydro-9H-imidazo[1,2-a]indol-2-one.

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Authors
  1. A. Sackus
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  2. V. Amankaviciene
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  3. V. Martynaitis
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Additional information

Department of Organic Chemistry, Kaunas University of Technology, LT-3028 Kaunas, Lithuania Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 761–769, June, 2000.

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Sackus, A., Amankaviciene, V. & Martynaitis, V. Condensation of 1-carbamoylmethyl-2,3,3-trimethyl-3H-indolium chloride with aromatic aldehydes. Chem Heterocycl Compd 36, 663–671 (2000). https://doi.org/10.1007/BF02297674

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  • DOI: https://doi.org/10.1007/BF02297674

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