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Synthesis of Bis-[3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene]acetamides by the Ritter Reaction and Their Properties

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Abstract

The Ritter reaction of dialkyl(benzyl)carbinols with N,N′-bis(cyanoacetyl)polymethylenediamines at a ratio of 2:1 (60–70°C, toluene/H2SO4) afforded N,N′-bis{[3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene]­acetyl}polymethylenediamines. The initial benzylcarbinols were 2-methyl-3-phenylpropan-1-ol, 3-(6,7-di­methoxyphenyl)-2-methylpropan-1-ol, 1-benzylcyclopentan-1-ol, 1-benzylcyclohexan-1-ol, and 2-methyl-3-(naphthalen-1-yl)propan-1-ol, and bis-cyanoacetamides were prepared from polyethylenediamines of the general formula H2N(CH2)nNH2 (n = 4–6), as well as piperazine. The synthesized compounds have enamino amide structure and exhibit nucleophilic properties; in particular, they reacted with phenyl isocyanate.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, 614990, Perm, Russia

    A. G. Mikhailovskii, E. S. Lichtenshtein & N. N. Pershina

  2. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    N. G. Kolotyrkina

Authors
  1. A. G. Mikhailovskii
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  2. E. S. Lichtenshtein
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  3. N. N. Pershina
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  4. N. G. Kolotyrkina
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Correspondence to A. G. Mikhailovskii.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 1, pp. 82–88 https://doi.org/10.31857/S0514749222010086.

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Mikhailovskii, A.G., Lichtenshtein, E.S., Pershina, N.N. et al. Synthesis of Bis-[3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene]acetamides by the Ritter Reaction and Their Properties. Russ J Org Chem 58, 65–69 (2022). https://doi.org/10.1134/S1070428022010080

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  • DOI: https://doi.org/10.1134/S1070428022010080

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