Synthesis of a Novel Series of 1,6-Disubstituted-3-(cyclohexylmethoxy)-β-carboline Derivatives via Minisci Reaction

Abstract

A facile and efficient route for the synthesis of 1,6-disubstituted-3-cyclohexylmethoxy-β-carboline derivatives via the Minisci reaction has been described with good yields and selectivity. A novel series of β-carboline derivatives with various substituents at 1-, 3-, and 6-positions were designed and synthesized from the starting material (±)-tryptophan on the basis of harmine chemical structure. The mechanism of the 1-substituted β-carboline derivatives by means of a nucleophilic radical was also described, and the x-ray analysis confirmed the structures of 11-7.

GRAPHICAL ABSTRACT

Keywords:

• β-Carboline
• electron-withdrawing
• harmine
• synthesis
• x-ray

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (No. 30973609), the Natural Science Foundation of Jiangsu Province (Program No. BK2009303), the Fundamental Research Funds for the Central Universities (Program No. 2J10004), and Specialized Research Fund for the Doctoral Program of Higher Education (Program No. 20100096110007) for financial support. This study was also supported by the Project Program of State Key Laboratory of Natural Medicines, China Pharmaceutical University (No. JKGP201105).

Notes

^a Determined with a digital melting-point apparatus and reported uncorrected.

^b Isolated yield by column chromatography.