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Monatshefte für Chemie - Chemical Monthly

, Volume 140, Issue 3, pp 339–348 | Cite as

Modular access to heterocycles: methyl 3-aminobenzo[b]thiophene-2-carboxylate–thiourea linkage or pyrimidine-4-one-2-thione formation

  • Jolanta RousseauEmail author
  • Vilija Kriščiūnienė
  • Ilona Rimkevičiūtė
  • Cyril Rousseau
  • Virginė Amankavičienė
  • Algirdas Šačkus
  • Arnaud Tatibouët
  • Patrick Rollin
Original Paper

Abstract

Modular conditions for the formation of thioureas or pyrimidine-4-one-2-thiones connected to the benzo[b]thiophene, benzene and indole structures were performed. A benzo[b]thiophene isothiocyanate derivative was used as a model to study the condensation with simple aromatic amines and amino-l-sorbose derivative. The construction of pyrimidine-4-one-2-thiones using basic conditions afforded efficiently new heterocyclic aromatics, which were further transformed using the alkylated sulfur as a leaving group in palladium-catalyzed cross-coupling reactions.

Graphical abstract

Keywords

Amino acids Carbohydrates Cyclizations Heterocycles Homogeneous catalysis 

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Copyright information

© Springer-Verlag 2008

Authors and Affiliations

  • Jolanta Rousseau
    • 1
    Email author
  • Vilija Kriščiūnienė
    • 1
  • Ilona Rimkevičiūtė
    • 1
  • Cyril Rousseau
    • 1
  • Virginė Amankavičienė
    • 1
  • Algirdas Šačkus
    • 1
  • Arnaud Tatibouët
    • 2
  • Patrick Rollin
    • 2
  1. 1.Department of Organic ChemistryKaunas University of TechnologyKaunasLithuania
  2. 2.I.C.O.A–UMR 6005Université d’OrléansOrléansFrance

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