Monatshefte für Chemie / Chemical Monthly

, Volume 126, Issue 8–9, pp 945–952 | Cite as

Synthesis of dihydrothiopyrano[3,4-c]pyridines and of fusion products thereof

  • F. Sauter
  • J. Fröhlich
  • E. K. Ahmed
Organische Chemie Und Biochemie

Summary

Reaction of the 6-hydroxy-thiopyrano[3,4-c]pyridine-5-carbonitrile derivative2 with α-halogeno-carbonyl compounds gave the O-substituted intermediates3a–d which on treatment with base were converted into the furo[2,3-b]thiopyrano[4,3-d]pyridines4a–d by fusion of a furan moiety. Cyclization of the corresponding ester4d led to fusion of a pyrimidine ring, thus yielding the tetracyclic product8 as well as its N-substituted derivatives9a–e. Target compounds2–9 were derived from the three novel heterocyclic parent systemsA–C.

Keywords

Fused S,N-heterocycles Fused S,N,O-heterocycles Thiopyrano[3,4-c]pyridine Furo[2,3-b]thiopyrano[4,3-d]pyridines Thiopyrano[4′',3′':4′,5′]pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine derivatives 

Synthese von Dihydrothiopyrano[3,4-c]pyridinen und ihrer Kondensationsprodukte

Zusammenfassung

Reaktion des 6-Hydroxy-thiopyrano[3,4-c]pyridin-5-carbonsäurenitril — Derivates2 mit α-Halogencarbonylverbindungen führte über die entsprechenden O-substituierten Zwischenprodukte3a–d durch Furan-Anellierungen zu den Furo[2,3-b]thiopyrano[4,3-d]pyridin — Derivaten4a–d. Cyclisierung des entsprechenden Esters4d gab unter Pyrimidin-Anellierung das tetracyclische Produkt8 sowie dessen N-Substitutionsprodukte9a–e. Die Zielverbindungen2–9 leiten sich von den drei neuen heterocyclischen GrundkörpernA–C ab.

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References

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    Sauter F, Jordis U, Fröhlich J, Gewald K, Grohmann F, Ahmed EK (1994) ACH-Models in Chemistry131: 489Google Scholar
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  8. [8]
    Van der Baan JL, Bickelhaupt F (1974) Tetrahedron30: 2447Google Scholar

Copyright information

© Springer-Verlag 1995

Authors and Affiliations

  • F. Sauter
    • 1
  • J. Fröhlich
    • 1
  • E. K. Ahmed
    • 1
  1. 1.Institute of Organic ChemistryTechnical University ViennaVienna

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