Synthesis of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)acetohydrazides via the Ritter reaction

The Ritter cyclocondensation of 2-methyl-1-phenylpropan-2-ols with cyanoacetohydrazide hydrazones in PhMe–H2SO4 medium at 60–70°С for 20 min resulted in the formation of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)-acetohydrazides. The product of β-C-carbamoylation of the enamine moiety was also obtained.

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Correspondence to Alexander G. Mikhailovskii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(5), 562–565

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Mikhailovskii, A.G., Pogorelova, E.S. & Pershina, N.N. Synthesis of N-benzylidene- and N-alkylidene(3,3-dialkyl-3,4-dihydroisoquinolin-1(2H)-ylidene)acetohydrazides via the Ritter reaction. Chem Heterocycl Comp 56, 562–565 (2020). https://doi.org/10.1007/s10593-020-02700-w

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Keywords

  • cyanoacetylhydrazide hydrazones
  • 3,4-dihydroisoquinolines
  • enamines
  • Ritter cyclization