Oxo-heterocyclic fused naphthalimides as antitumor agents: synthesis and biological evaluation

Shaoying Tan1, Hong Yin, Zhuo Chen

  • 1State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China.

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
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Preparation of Amines: Reduction of Oximes and Nitro Compounds

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