Synthesis of 2,3-Disubstituted 4-Ethoxycarbonyl-β-carbolin-1-ones: Application to the Synthesis of SL651498 and Its Analogue

Ryoya Miura; Shinsuke Goto; Takahide Hashimoto; Iwao Hachiya

doi:10.1021/acsomega.0c01854

Synthesis of 2,3-Disubstituted 4-Ethoxycarbonyl-β-carbolin-1-ones: Application to the Synthesis of SL651498 and Its Analogue

ACS Omega. 2020 Jun 16;5(25):15631-15656. doi: 10.1021/acsomega.0c01854. eCollection 2020 Jun 30.

Authors

Ryoya Miura¹, Shinsuke Goto¹, Takahide Hashimoto¹, Iwao Hachiya¹

Affiliation

¹ Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu Mie 514-8507, Japan.

Abstract

Synthesis of 2,3-disubstituted 4-ethoxycarbonyl-β-carbolin-1-ones is developed using palladium-catalyzed intramolecular amination of 3-amino-4-(2-bromophenyl)-2-pyridones prepared by the conjugate addition reaction of diethyl 2-aminomalonate to alkynyl imines. The method was applied to the total syntheses of SL651498 exhibiting anxiolytic activity and its analogue.