121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-422
Subject Synthesis of Benzo[a]carbazole Derivatives via imino-Stetter reaction
Authors Jiye Jeon, Cheol-Hong Cheon*
Department of Chemistry, Korea University, Korea
Abstract Benzo[a]carbazole has received considerable attentions from the chemical society due to their interesting biological and pharmacological activities. For example, they have been known to be used as drug precursors with anticanceral and antibacterial activities. In addition, they exhibit estrogen receptor binding affinities. Furthermore, they have been utilized in the field of materials science, such as organic light-emitting diodes and dye-sensitized solar cell. Thus, many methods for synthesis of benzo[a]carbazole have been developed so far. However, considering the importance of these compounds, the development of new synthetic method is still needed. Herein we will describe the new protocol to access these scaffolds using imino-Stetter reaction as the key step. We recently developed efficient method for the synthesis of 2-substituted indole-3-acetic acid derivatives from aldimines derived from 2-aminocinnamic acid derivatives and aldehydes via intramolecular imino-Stetter reaction using cyanide as the catalyst.1 We envisioned that 2-arylindole derivatives bearing a β-ketone moiety at the 3-position could be obtained via imino-Stetter reaction from aldimines derived from 2-aminochalcone derivatives and aldehydes. Subsequent intramolecular Friedel-Crafts reaction under acidic conditions would furnish benzo[a]carbazole scaffolds. In this poster presentation, we will disclose our new approach for synthesis the benzo[a]carbazoles. Furthermore, limitation and solutions of our protocol will be also discussed. References 1. (a) Lee, S. J.; Seo, H.-A.; Cheon, C.-H. Adv. Synth. Catal. 2016, 358, 1566. (b) Seo, H.-A.; Cheon, C.-H. J. Org. Chem. 2016, 81, 7917.
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