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

Ekaterina Shinkevich, Jurgen Deblander, Sandra Matthijs, Jan Jacobs UGent, Norbert De Kimpe UGent and Kourosch Abbaspour Tehrani (2011) ORGANIC & BIOMOLECULAR CHEMISTRY. 9(2). p.538-548
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.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
SOLID-PHASE SYNTHESIS, PICTET-SPENGLER REACTION, INDOLE ALKALOIDS, CONDENSATION, ISOQUINOLINE, DERIVATIVES, TRICHLOROACETAMIDE, REARRANGEMENT, CYCLIZATION, CHEMISTRY
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
9
issue
2
pages
538 - 548
Web of Science type
Article
Web of Science id
000285749800031
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.696 (2011)
JCR rank
11/56 (2011)
JCR quartile
1 (2011)
ISSN
1477-0520
DOI
10.1039/c0ob00391c
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1265583
handle
http://hdl.handle.net/1854/LU-1265583
date created
2011-06-16 11:19:35
date last changed
2011-06-20 16:25:05
@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},
}

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.