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Synthesis of heterocyclic compounds from the products of addition of polyhaloalkanes to unsaturated systems 4. Synthesis of substituted furo[2,3-d]pyrimidines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Amino-5-methyl-4-(2,2,2-trichloroethyl)-3-furonitrile was synthesized from 3,5,5,5-tetrachloropentan-2-one, a product of the radical addition of CCl4 to methyl vinyl ketone, according to a scheme known for α-haloketones. The product was converted via the corresponding imino-ether into N2-substituted N1 [5-methyl-4-(2,2,2-trichloroethyl)-3-cyano-2-furyl]formamidines. Cyclization of these formamidines gave 2-methyl-3-(2,2,2-trichloroethyl)-5-R-4-imino-4,5-dihydrofuro[2,3-d]pyrimidines, which readily regroup according to Dimroth into 2-methyl-3-(2,2,2-trichloroethyl)-4-R-aminofuro[2,3-d]pyrimidines.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913, Moscow

    L. I. Belen'kii, D. M. Antonov, A. A. Dudinov, E. D. Lubuzh & M. M. Krayushkin

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  1. L. I. Belen'kii
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  2. D. M. Antonov
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  3. A. A. Dudinov
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  4. E. D. Lubuzh
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  5. M. M. Krayushkin
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Additional information

For communication 3, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 124–129, January, 1993.

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Belen'kii, L.I., Antonov, D.M., Dudinov, A.A. et al. Synthesis of heterocyclic compounds from the products of addition of polyhaloalkanes to unsaturated systems 4. Synthesis of substituted furo[2,3-d]pyrimidines. Chem Heterocycl Compd 29, 109–114 (1993). https://doi.org/10.1007/BF00528647

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  • DOI: https://doi.org/10.1007/BF00528647

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