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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Preparation and Photophysical Characterization of N‑Substituted 7‑Nitro-2,1,3-benzoxadiazol-4-amine Derivatives

Jeremy P Bard1, Audrey K MacNair1, Tiyaba J Jamil1

  • 1Department of Chemistry, Washington College, Chestertown, Maryland 21620, United States.

ACS Omega
|November 3, 2025
PubMed

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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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.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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