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Synthesis of (-)-DAPD

Marcos L Sznaidman1, Jinfa Du, Amir Pesyan

  • 1Division of Organic Chemistry, Triangle Pharmaceuticals Inc., Durham, North Carolina, USA. msznaidman@norakbio.com

Nucleosides, Nucleotides & Nucleic Acids
|January 5, 2005
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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.