Synthesis of 2-nitroindoles via the Sundberg indole synthesis

✍ Scribed by Erin T. Pelkey; Gordon W. Gribble

• Book ID: 104257626
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 178 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)01272-0

✦ Synopsis

A three-step sequence has been developed for converting o-nitrobenzaldehydes into 2nitroindoles. The key step involves the thermolysis of 2-(o-azidophenyl)nigoethylene (10) in xylenes which gives 2-nitroindole (4) in 54% yield, akin to the classic Sundberg indole synthesis. This p~ure has also been utilized to synthesize 5,6-dimethoxy-2-nitroindole ( 14).