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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Published on: February 15, 2016

Development of 3-aryl-1-isoquinolinamines as potent antitumor agents based on CoMFA

Su Hui Yang1, Hue Thi My Van, Thanh Nguyen Le

  • 1College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Buk-gu, Gwangju 500-757, Korea.

European Journal of Medicinal Chemistry
|September 7, 2010
PubMed

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Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
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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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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.