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Synthesis of quinoid natural products and analogues

Blaise Mbala-Mavinga UGent (2011)
abstract
Quinones are important structural cores for the discovery and development of new drugs. Due to their wide spectrum of biological activity, quinones keep on arising considerable interests to synthetic and medicinal chemists. The present PhD dissertation is an account of a contribution on a series of syntheses of naturally occurring quinones and their analogues. It particularly covers the continuing efforts towards the synthesis of 2-azaanthraquinone and naphthyridinone alkaloids. In this respect, the results of synthetic projects are disclosed. A first part discloses the synthesis of 2-azasampangine starting from 2-azacleistopholine. The preparation of 2-azacleistopholine was accomplished under ligand-free Heck and Pomeranz-Fritsch reaction conditions. The obtained 2-azacleistopholine was smoothly converted to 4-[2-(dimethyl)aminovinyl]benzo[g]isoquinoline. The synthesis of 2-azasampangine is still in progress. The second part deals with the synthesis of 2-azaanthraquinones substituted at the C-1 peri-carbonyl position and linked to phenyl groups through a biaryl axis. Thanks to the efficiency of pyridium ylid chemisty, the syntheses of 2-azaanthraquinones were smoothly accomplished in moderate to good yield. However, The difficult access to 2-azaanthraquinones through the direct utilization of the Nenitzescu reaction led to an investigation towards the synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones. Therefore, three synthetic routes were explored. The route utilizing the oxidative addition of enaminoesters to the 1,4-dihydroxy-2-methoxycarboxynaphthalene was the best one and gave the targeted 2,3-disubstituted 1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylates in low to good yields.
Please use this url to cite or link to this publication:
author
promoter
UGent
organization
alternative title
Synthese van chinoïde natuurproducten en analogen
year
type
dissertation (monograph)
subject
keyword
azaanthraquinones, qunoid natural products, naphthyridines
pages
VIII, 151 pages
publisher
Ghent University. Faculty of Bioscience Engineering
place of publication
Ghent, Belgium
defense location
Gent : Faculteit Bio-ingenieurswetenschappen (A0.030)
defense date
2011-10-25 16:30
ISBN
9789059894730
language
English
UGent publication?
yes
classification
D1
copyright statement
I have retained and own the full copyright for this publication
id
1932713
handle
http://hdl.handle.net/1854/LU-1932713
date created
2011-10-19 12:25:23
date last changed
2011-10-20 13:27:09
@phdthesis{1932713,
  abstract     = {Quinones  are important structural cores for the discovery and development of new drugs. Due to their wide spectrum of biological activity, quinones keep on arising considerable interests to synthetic and medicinal chemists. 
The present PhD dissertation is an account of a contribution on a series of syntheses of naturally occurring quinones and their analogues. It particularly covers the continuing efforts towards the synthesis of 2-azaanthraquinone and naphthyridinone alkaloids. In this respect, the results of synthetic projects are disclosed. 
A first part discloses the synthesis of 2-azasampangine starting from 2-azacleistopholine. The preparation of 2-azacleistopholine was accomplished under ligand-free Heck and Pomeranz-Fritsch reaction conditions. The obtained 2-azacleistopholine was smoothly converted to 4-[2-(dimethyl)aminovinyl]benzo[g]isoquinoline. The synthesis of 2-azasampangine is still in progress. 
The second part deals with the synthesis of 2-azaanthraquinones substituted at the C-1 peri-carbonyl position and linked to phenyl groups through a biaryl axis. Thanks to the efficiency of pyridium ylid chemisty, the syntheses of 2-azaanthraquinones were smoothly accomplished in moderate to good yield. However, The difficult access to 2-azaanthraquinones  through the direct utilization of the Nenitzescu reaction led to an investigation towards the synthesis of benzo[g]isoquinoline-1,5,10(2H)-triones. Therefore, three synthetic routes were explored. The route utilizing the oxidative addition of enaminoesters to the 1,4-dihydroxy-2-methoxycarboxynaphthalene was the best one and gave the targeted 2,3-disubstituted 1,2,5,10-tetrahydro-1,5,10-trioxobenzo[g]isoquinoline-4-carboxylates  in low to good yields.},
  author       = {Mbala-Mavinga, Blaise},
  isbn         = {9789059894730},
  keyword      = {azaanthraquinones,qunoid natural products,naphthyridines},
  language     = {eng},
  pages        = {VIII, 151},
  publisher    = {Ghent University. Faculty of Bioscience Engineering},
  school       = {Ghent University},
  title        = {Synthesis of quinoid natural products and analogues},
  year         = {2011},
}

Chicago
Mbala-Mavinga, Blaise. 2011. “Synthesis of Quinoid Natural Products and Analogues”. Ghent, Belgium: Ghent University. Faculty of Bioscience Engineering.
APA
Mbala-Mavinga, B. (2011). Synthesis of quinoid natural products and analogues. Ghent University. Faculty of Bioscience Engineering, Ghent, Belgium.
Vancouver
1.
Mbala-Mavinga B. Synthesis of quinoid natural products and analogues. [Ghent, Belgium]: Ghent University. Faculty of Bioscience Engineering; 2011.
MLA
Mbala-Mavinga, Blaise. “Synthesis of Quinoid Natural Products and Analogues.” 2011 : n. pag. Print.