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Reaction of isopropylidene malonate with N-arylidene-2-naphthylamines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown that 4-aryl-2-oxo-1,2,3,4-tetrahydro-5,6-benzoquinolines are formed in the reaction of N-arylidene-2-naphthylamines with isopropylidene malonate. The reaction takes place with cleavage of the isopropylidene malonate ring and the production of carbon dioxide and acetone. The structure of the benzotetrahydroquinolines obtained were confirmed by identification of the compound obtained by sulfur dehydrogenation of the product of the reaction of isopropylidene malonate with arylidenenaphthylamine (aryl=phenyl) with an authentic sample of 1,2-dihydro-2-oxo-4-phenyl-5,6-benzoquinoline and of the reaction product (in which the aryl group was absent) with an authentic sample of 2-oxo-1,2,3,4-tetrahydro-5,6-benzoquinoline. The IR and PMR spectra data are presented.

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Authors and Affiliations

  1. Riga Polytechnic Institute, 226355, Riga

    Ya. A. Strods, R. B. Kampare, I. é. Lielbriedis & O. Ya. Neiland

Authors
  1. Ya. A. Strods
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  2. R. B. Kampare
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  3. I. é. Lielbriedis
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  4. O. Ya. Neiland
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 973–976, July, 1977.

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Strods, Y.A., Kampare, R.B., Lielbriedis, I.é. et al. Reaction of isopropylidene malonate with N-arylidene-2-naphthylamines. Chem Heterocycl Compd 13, 788–791 (1977). https://doi.org/10.1007/BF00470203

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  • DOI: https://doi.org/10.1007/BF00470203

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