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Reaction of 10-formyl-3-methyl-1,2,3,4-tetrahydropyrimido [1,2-a]indole and its dimethyliminium salt with nucleophilic agents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 10-dimethyliminium-3-methyl-1,2,3,4-tetrahydropyrimido[1,2-a] indole chloride and the protonated form of 10-formyl-3-methyl-1,2,3,4-tetrahydropyrimido[1,2-a]indole with some N- and C-nucleophiles leads to the formation of products of condensation at the carbonyl carbon atom. Condensation with the potassium enolate of cyanoacetic ester is accompanied by subsequent cyclization to give compounds of the α-carboline series. Acidic hydrolysis of the aldehyde gives 3-methyl-1,2,3,4-tetrahydropyrimido[1,2]indole hydrochloride.

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    B. I. Gorin, G. A. Golubeva, E. S. Besidskii, L. A. Sviridova & Yu. G. Bundel'

Authors
  1. B. I. Gorin
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  2. G. A. Golubeva
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  3. E. S. Besidskii
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  4. L. A. Sviridova
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  5. Yu. G. Bundel'
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 630–634, May, 1983.

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Gorin, B.I., Golubeva, G.A., Besidskii, E.S. et al. Reaction of 10-formyl-3-methyl-1,2,3,4-tetrahydropyrimido [1,2-a]indole and its dimethyliminium salt with nucleophilic agents. Chem Heterocycl Compd 19, 507–511 (1983). https://doi.org/10.1007/BF00514459

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  • DOI: https://doi.org/10.1007/BF00514459

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