Advertisement

Monatshefte für Chemie / Chemical Monthly

, Volume 109, Issue 1, pp 53–61 | Cite as

Imidazo- und Diazino-Anellierungen an das [1]Benzothieno[2,3—d]pyrimidin-System

  • Fritz Sauter
  • Peter Stanetty
  • Eike Schrom
  • Gerhard Sengstschmid
Organische Chemie und Biochemie

Imidazo- and diazino-anellations to the [1]benzothieno[2,3-d]-pyrimidine system

Abstract

Derivatives of the following six ring systems were synthesized:
  1. 1.

    3,10-Dihydro-[1]benzothieno[2,3-d]imidazo[1,5-a]-pyrimidine (I)

     
  2. 2.

    6H-[1]Benzothieno[2,3-d]pyrazino[1,2-a]pyrimidine (II)

     
  3. 3.

    1,5-Dihydro-[1]benzothieno[2,3-d]imidazo[1,2-a]-pyrimidine (III)

     
  4. 4.

    6H-[1]Benzothieno[2,3-d]pyrimido[1,2-a]pyrimidine (IV)

     
  5. 5.

    1,5-Dihydro-imidazo[1,2-a]thieno[2,3-d]pyrimidine (V)

     
  6. 6.

    4H-Pyrimido[1,2-a]thieno[2,3-d]pyrimidine (VI)

     

The first four types are new heterocyclic systems. 2-Aminomethyl-5,6,7,8-tetrahydro-[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (5), which was used as intermediate for typesI andII, was synthesized by various methods. TypesIII andIV were prepared from 2-methylthio-5,6,7,8-tetrahydro-[1]-benzothieno[2,3-d]pyrimidin-4(3H)-one via the corresponding 2-benzylamino derivatives, followed by ring closure.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. 1.
    Thiazolo-Anellierung an dera-Kante: 4H-Thiazolo[3,2-a]thieno[3,2-e]-pyrimidin und 5H-[1]Benzothieno[3,2-e]thiazolo[3,2-a]pyrimidin:F. Sauter undW. Deinhammer, Mh. Chem.105, 452 (1974);F. Sauter, W. Deinhammer undP. Stanetty, Mh. Chem.105, 1258 (1974).Google Scholar
  2. 2a).
    Thiazolo-Anellierung an derb-Kante: 5H-Thiazolo[3,2-a]thieno-[2,3-d]pyrimidin und 5H-[1]Benzothieno[2,3-d]thiazolo[3,2-a]pyrimidin: wie bei1, zusätzlichF. Sauter, W. Deinhammer undK. Danksagmüller, Mh. Chem.105, 863 und 882 (1974);Google Scholar
  3. 2b).
    Triazolo-Anellierung an derb-Kante: 1,5-Dihydro-thieno[2,3-d]-1,2,4-triazolo[1,5-a]pyrimidin und 1,5-Dihydro-[1]benzothieno[2,3-d]-1,2,4-triazolo[1,5-a]-pyrimidin:F. Sauter undW. Deinhammer, Mh. Chem.105, 558 (1974);Google Scholar
  4. 2c).
    Benzisothiazolo-Anellierung an derb-Kante: 4H-Thieno[2′,3′:4,5]-pyrimido[1,2-b][1,2]benzisothiazol und 13H-[1]Benzothieno[2′,3′: 4,5]-pyrimido[1,2-b][1,2]benzisothiazol:F. Sauter undW. Deinhammer, Mh. Chem.105, 1249 (1974).Google Scholar
  5. 3.
    Triazolo-Anellierung an derc-Kante: [1]Benzothieno[3,2-e]-1,2,4-triazolo[2,3-c]pyrimidin:F. Sauter undP. Stanetty, Mh. Chem.106, 1111 (1975).Google Scholar
  6. 4.
    P. Blaszkiewicz, H. Vorbrueggen undH. J. Kessler (Schering AG), Deutsche Offenlegungsschrift 2 411 274 (18. Sept. 1975).Google Scholar
  7. 5.
    P. Blaszkiewicz, H. Vorbrueggen undH. Koch (Schering AG), Deutsche Offenlegungsschrift 2 411 273 (18. Sept. 1975).Google Scholar
  8. 6.
    F. Sauter, P. Stanetty undE. Schrom, Arch. Pharm.310, 337 (1977).Google Scholar
  9. 7.
    K. Gewald, Chem. Ber.99, 94 (1966).Google Scholar
  10. 8.
    F. Sauter, Mh. Chem.99, 2100 (1968).Google Scholar
  11. 9.
    P. Stanetty, Publikation in Vorbereitung.Google Scholar
  12. 10.
    F. Sauter undW. Deinhammer, Mh. Chem.105, 558 (1974).Google Scholar

Copyright information

© Springer-Verlag 1978

Authors and Affiliations

  • Fritz Sauter
    • 1
  • Peter Stanetty
    • 1
  • Eike Schrom
    • 1
  • Gerhard Sengstschmid
    • 1
  1. 1.Institut für Organische ChemieTechnische Universität WienWienÖsterreich

Personalised recommendations