Advanced search
1 file | 320.29 KB

Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones

Author
Organization
Abstract
1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated Pictet-Spengler reaction of the corresponding imines of 2-(1,4-dimethoxynaphth-2-yl)ethylamine in the presence of an acyl chloride and AlCl3 followed by an oxidation with silver(II) oxide in nitric acid. Depending on the reaction conditions the N-trichloroacetyl protecting group could be cleaved off, converted to an N-methoxycarbonyl group or transformed to an N-(2-oxoacetamide) moiety. The synthesized 1,2-disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones constitute a new class of quinones, which has not been reported yet.
Keywords
SOLID-PHASE SYNTHESIS, PICTET-SPENGLER REACTION, INDOLE ALKALOIDS, CONDENSATION, ISOQUINOLINE, DERIVATIVES, TRICHLOROACETAMIDE, REARRANGEMENT, CYCLIZATION, CHEMISTRY

Downloads

  • (...).pdf
    • full text
    • |
    • UGent only
    • |
    • PDF
    • |
    • 320.29 KB

Citation

Please use this url to cite or link to this publication:

Chicago
Shinkevich, Ekaterina, Jurgen Deblander, Sandra Matthijs, Jan Jacobs, Norbert De Kimpe, and Kourosch Abbaspour Tehrani. 2011. “Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones.” Organic & Biomolecular Chemistry 9 (2): 538–548.
APA
Shinkevich, E., Deblander, J., Matthijs, S., Jacobs, J., De Kimpe, N., & Abbaspour Tehrani, K. (2011). Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones. ORGANIC & BIOMOLECULAR CHEMISTRY, 9(2), 538–548.
Vancouver
1.
Shinkevich E, Deblander J, Matthijs S, Jacobs J, De Kimpe N, Abbaspour Tehrani K. Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones. ORGANIC & BIOMOLECULAR CHEMISTRY. 2011;9(2):538–48.
MLA
Shinkevich, Ekaterina, Jurgen Deblander, Sandra Matthijs, et al. “Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones.” ORGANIC & BIOMOLECULAR CHEMISTRY 9.2 (2011): 538–548. Print.
@article{1265583,
  abstract     = {1,2-Disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones are prepared for the first time through an activated Pictet-Spengler reaction of the corresponding imines of 2-(1,4-dimethoxynaphth-2-yl)ethylamine in the presence of an acyl chloride and AlCl3 followed by an oxidation with silver(II) oxide in nitric acid. Depending on the reaction conditions the N-trichloroacetyl protecting group could be cleaved off, converted to an N-methoxycarbonyl group or transformed to an N-(2-oxoacetamide) moiety. The synthesized 1,2-disubstituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones constitute a new class of quinones, which has not been reported yet.},
  author       = {Shinkevich, Ekaterina and Deblander, Jurgen and Matthijs, Sandra and Jacobs, Jan and De Kimpe, Norbert and Abbaspour Tehrani, Kourosch},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {SOLID-PHASE SYNTHESIS,PICTET-SPENGLER REACTION,INDOLE ALKALOIDS,CONDENSATION,ISOQUINOLINE,DERIVATIVES,TRICHLOROACETAMIDE,REARRANGEMENT,CYCLIZATION,CHEMISTRY},
  language     = {eng},
  number       = {2},
  pages        = {538--548},
  title        = {Synthesis of 1-substituted 1,2,3,4-tetrahydrobenz[g]isoquinoline-5,10-diones},
  url          = {http://dx.doi.org/10.1039/c0ob00391c},
  volume       = {9},
  year         = {2011},
}

Altmetric
View in Altmetric
Web of Science
Times cited: