Rapid, microwave-assisted synthesis of N1-substituted 3-amino-1,2,4-triazoles

✍ Scribed by Jerry Meng; Pei-Pei Kung

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 225 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.12.042

✦ Synopsis

A robust, regioselective synthesis of 3-amino-1,2,4-triazoles is described. This reaction employs a key intermediate 2, which is coupled to carboxylic acids in good yields to afford intermediates 3a-d. These entities, in turn, react with a variety of hydrazines or hydrazine hydrochlorides to provide proposed intermediates 4a-j, which under microwave conditions cyclize to the desired 3-amino-1,2,4-triazoles (compounds 5a-j). This approach permits the rapid synthesis of regioselective N1-substituted 3-amino-1,2,4-triazoles, and is shown to afford a variety of such compounds in 34-70% isolated yields.