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Synthesis of quinoid natural products and analogues

(2011)
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(UGent)
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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.
Keywords
azaanthraquinones, qunoid natural products, naphthyridines

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Citation

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MLA
Mbala-Mavinga, Blaise. Synthesis of Quinoid Natural Products and Analogues. Ghent University. Faculty of Bioscience Engineering, 2011.
APA
Mbala-Mavinga, B. (2011). Synthesis of quinoid natural products and analogues. Ghent University. Faculty of Bioscience Engineering, Ghent, Belgium.
Chicago author-date
Mbala-Mavinga, Blaise. 2011. “Synthesis of Quinoid Natural Products and Analogues.” Ghent, Belgium: Ghent University. Faculty of Bioscience Engineering.
Chicago author-date (all authors)
Mbala-Mavinga, Blaise. 2011. “Synthesis of Quinoid Natural Products and Analogues.” Ghent, Belgium: Ghent University. Faculty of Bioscience Engineering.
Vancouver
1.
Mbala-Mavinga B. Synthesis of quinoid natural products and analogues. [Ghent, Belgium]: Ghent University. Faculty of Bioscience Engineering; 2011.
IEEE
[1]
B. Mbala-Mavinga, “Synthesis of quinoid natural products and analogues,” Ghent University. Faculty of Bioscience Engineering, Ghent, Belgium, 2011.
@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},
  keywords     = {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},
}