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

ML Rosenberg, JHF Aasheim, M Trebbin, E Uggerud…

Index: Rosenberg, Marianne Lenes; Aasheim, Jens H. F.; Trebbin, Martin; Uggerud, Einar; Hansen, Tore Tetrahedron Letters, 2009 , vol. 50, # 47 p. 6506 - 6508

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Citation Number: 6

Abstract

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.