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Updated: Jul 25, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Pyrroloindoline/Pyridoindoline Synthesis via C3-Dearomative Arylation/Cyclization of Tryptamine/Homotryptamine
Miyuki Yamaguchi1, Ryoya Hagiwara1, Hana Muto1
1School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Abstract:
A palladium-dihydroxyterphenylphosphine (DHTP) catalyst was successfully applied to the dearomative C3-arylation of tryptamine derivatives with aryl nonaflates. The intramolecular cyclization of the resulting 3,3-disubstituted indolenines afforded C3a-arylated pyrroloindolines in one pot. We postulate that the formation of complexes between the lithium salts of DHTP and the tryptamine derivative is the key to promoting selective arylation at the C3-position of the indole ring. Furthermore, reactions using homotryptamine derivatives successfully provided C4a-arylated pyridoindolines.
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