Synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoester

✍ Scribed by Marianne Lenes Rosenberg; Jens H.F. Aasheim; Martin Trebbin; Einar Uggerud; Tore Hansen

• Book ID: 104096947
• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 237 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.09.032

✦ Synopsis

Pd(OAc) 2 -catalyzed decomposition of ethyl 2-diazo-4-(4-indolyl)-3-oxobutanoate leads to a tricyclic tetrahydrobenzindole compound formed by a formal C-H insertion reaction. This tricyclic indole rearranges to a novel and thermodynamically more stable naphthalene derivative. Treatment of N-tosyl-protected ethyl 2-diazo-4-(4-indolyl)-3-oxobutanoate with a base induces facile pyrazole formation.