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Monatshefte für Chemie / Chemical Monthly

, Volume 124, Issue 11–12, pp 1225–1227 | Cite as

Naturstoffchemie, 171. Mitt.: Verhalten von Ethyl-(E)-3-(4-brom-3-methylbut-2-enyl)-N-methyl-1,2,3,4-tetrahydro-3-chinolin-2,4(1H,3H)-dion-carboxylat in Anwesenheit von 1,8-Diazabicyclo[5,4,0]undec-7-en (DBU)

Kurze Mitteilung
  • Johannes Reisch
  • Marlies Iding
  • Ingo von Bassewitz
Organische Chemie Und Biochemie

Natural product chemistry, part 171: Behaviour of ethyl-(E)-3-(4-bromo-3-methylbut-2-enyl)-N-methyl-1,2,3,4-tetrahydro-3-quinolin-2,4(1H,3H)-dionecarboxylate in the presence of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU)

Summary

In the presence of pentaisopropylguanidine (PIG) ethyl-(E)-4-[(4-bromo-3-methylbut-2-enyl)-oxy]-N-methyl-3-quinolin-2(1H)-onecarboxylate was converted into diethyl-(E)-4,4′-[(2-methylbut-2-en-1,4-diyl)bis(oxy)]bis[1,2-dihydro-N-methyl-3-quinolin-2(1H)-onecarboxylate]. The reaction of ethyl-(E)-3-(4-bromo-3-methylbut-2-enyl)-N-methyl-1,2,3,4-tetrahydro-3-quinolin-2,4(1H,3H)-dionecarboxylate and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) gave the 2(1H)-quinolone alkaloid (±)-Almeine and 2,3,4,5,8,9-hexahydro-12-methyl-1H,7H,11H-azepeino[2′,1′:2,3]-pyrimido-[1,2-c]-[5,1,3]benzoxadiazocin-11,17(12H)-dione.

Keywords

Ethyl-(E)-4-[(4-bromo-3-methylbut-2-enyl)-oxy]-N-methyl-3-quinolin-2(1H)-onecarboxylate Pentaisopropylguanidine (PIGDiethyl-(E)-4,4′-[(2-methylbut-2-en-1,4-diyl)bis(oxy)]bis-[1,2-dihydro-N-methyl-3-quinolin-2(1H)-onecarboxylate] Ethyl-(E)-3-(4-bromo-3-methylbut-2-enyl)-N-methyl-1,2,3,4-tetrahydro-3-quinolin-2,4(1H,3H)-dionecarboxylate 1,8-Diazabicyclo[5,4,0]undec-7-ene (DBU(±)-Almeine 2,3,4,5,8,9-Hexahydro-12-methyl-1H,7H,11H-azepino[2′,1′:2,3]pyrimido[1,2-c][5,1,3])benzoxadiazocin-11,17(12H)-dione 

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Literatur

  1. [1]
    170. Mitteilung: Reisch J., Den Hertog H. J., Büse E., Kaiserling-Buddemeier I. (im Druck) Acta Pharm. TurcicaGoogle Scholar
  2. [2]
    Iding M. (1993) Teil der Dissertation. Universität MünsterGoogle Scholar
  3. [3]
    Von Bassewitz I. (1992) Teil der Diplomarbeit. Universität MünsterGoogle Scholar
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    Reisch J., Probst W., Iding M. (im Druck) Acta Pharm. TurcicaGoogle Scholar
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    Reisch J., Iding M., Von Bassewitz I. (1993) J. Heterocycl. Chem.30: 977Google Scholar
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    Reisch J., Iding M. (1989) Monatsh. Chem.119: 1169Google Scholar

Copyright information

© Springer-Verlag 1993

Authors and Affiliations

  • Johannes Reisch
    • 1
  • Marlies Iding
    • 1
  • Ingo von Bassewitz
    • 1
  1. 1.Institut für Pharmazeutische ChemieWestfälische Wilhelms-Universität MünsterMünsterBundesrepublik Deutschland

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