Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 462–463 | Cite as

Syntheses of di- and tetrahydropyrroles

IV. Synthesis of substituted 4-isopropyl-2-methyl- and 2,4,4-trimethyl-δ1-pyrrolines
  • V. M. Berezovskii
  • V. B. Spiro
  • L. Ya. Denisova
  • B. M. Sheiman


By the Michael's condensation of 3-methyl-1-nitro-1-butene with esters of α-acetoglutaric and acetosuccinic acids and of 2-methyl-1-nitropropene with acetylacetone we have synthesized the corresponding γ-nitrocarbonyl compounds, which have been converted by reductive cyclization into 3-ethoxycarbonyl-4-isopropyl-3-methoxycarbonylethyl-2-methyl-Δ1-pyrroline, 3-ethoxycarbonyl-3-ethoxycarbonylmethyl-4-isopropyl-2-methyl-Δ1-pyrroline, and 3-acetyl-2, 4, 4-trimethyl-Δ1-pyrroline, respectively.


Ester Organic Chemistry Acetylacetone Reductive Cyclization Tetrahydropyrroles 
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  1. 1.
    V. M. Berezovskii, V. B. Spiro, and B. M. Sheiman, KhGS [Chemistry of Heterocyclic Compounds], 4, 108, 1968.Google Scholar
  2. 2.
    B. M. Sheiman, V. B. Spiro, and V. M. Berezovskii, KhGS [Chemistry of Heterocyclic Compounds], 4, 111, 1968.Google Scholar
  3. 3.
    B. M. Sheiman, V. B. Spiro, N. B. Chernysheva, L. M. Smuilovich, I. M. Kustonavich, and V. M. Berezovskii, KhGS [Chemistry of Heterocyclic Compounds], 4, 624, 1968.Google Scholar
  4. 4.
    Organic Syntheses [Russian translation], IL, Moscow 10, 181, 1963.Google Scholar
  5. 5.
    C. T. Bahner, U.S. patent 2425276, 1947; C.A. 41, 7410, 1947.Google Scholar
  6. 6.
    C. T. Bahner, U.S. patent 2431451, 1947; C.A. 42, 2615, 1948.Google Scholar
  7. 7.
    R. Bonnett, V. M. Clark, A. Giddey, and A. Todd, J. Chem. Soc., 1959, 2087.Google Scholar
  8. 8.
    L. Bellamy, Infrared Spectra of Complex Molecules [Russian translation], IL, Moscow, 1963.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • V. M. Berezovskii
    • 1
  • V. B. Spiro
    • 1
  • L. Ya. Denisova
    • 1
  • B. M. Sheiman
    • 1
  1. 1.All-Union Scientific-Research Vitamin InstituteMoscow

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