Russian Chemical Bulletin

, Volume 49, Issue 9, pp 1634–1636 | Cite as

Synthesis of 3-hydroxy-1-methyl-2-(methylthio) pyrrole from methyl isothiocyanate and prop-2-yn-1-ol

  • L. Brandsma
  • N. A. Nedolya
  • B. A. Trofimov
Brief Communications

Abstract

A methylated adduct of lithiated 1-(1-ethoxyethoxy)allene and methyl isothiocyanate undergoes intramolecular cyclization in the presence of CuBr to give 3-(1-ethoxyethoxy)-1-methyl-2-(methylthio)pyrrole. The methanolysis of the latter affords 3-hydroxy-1-methyl-2-(methylthio)pyrrole.

Key words

prop-2-yn-1-ol ethoxyethene 1-(1-ethoxyethoxy)allene lithiation methyl isothiocyanate 2-(1-ethoxyethoxy)buta-2,3-dienimidothioate cyclization 3-hydroxy-1-methyl-2-(methylthio)pyrrole keto-enol tautomerism 

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References

  1. 1.
    N. A. Nedolya,Novel Chemistry Based on Isothiocyanates and Polar Organometallics, Thesis of Utrecht University (The Netherlands), 1999, 144 pp.Google Scholar
  2. 2.
    L. Brandsma and H. Verkruijsse,Preparative Polar Organometallic Chemistry, Springer Verlag, Berlin-Heidelberg-New York-London, 1987, 240 pp.Google Scholar
  3. 3.
    N. A. Nedolya, L. Brandsma, O. A. Tarasova, H. D. Verkruijsse, and B. A. Trofimov,Tetrahedron Lett., 1998,39, 2409.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 2000

Authors and Affiliations

  • L. Brandsma
    • 1
  • N. A. Nedolya
    • 2
  • B. A. Trofimov
    • 2
  1. 1.Department of Preparative Organic ChemistryUtrecht UniversityUtrechtThe Netherlands
  2. 2.A. E. Favorsky Irkutsk Institute of ChemistrySiberian Branch of the Russian Academy of SciencesIrkutskRussian Federation

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