A Study on the Phosphorylation of Indole, Imidazole, Carbazole, and Phenothiazine Derivatives

Abstract

N-Heterocycles including indolecarbaldehyde, substituted benzimidazoles, and methylimidazole could be efficiently phosphorylated by diethyl chlorophosphate at room temperature in different solvents using alkali carbonate or triethylamine as the base. However, the phosphorylation of N-heterocycles with a lower reactivity at the NH function, such as carbazole and phenothiazine, could not be conducted to complete conversion under the conditions applied.

Keywords:

• N-heterocycles
• phosphorylation
• indoles
• imidazoles
• carbazole
• phenothiazine

Acknowledgments

The authors are grateful to the Hungarian Scientific and Research Fund (OTKA K83118) for their support to this project. This work is connected to the scientific program of the “Development of quality-oriented and harmonized R+D+I strategy and functional model at BME” project. This project is supported by the New Széchenyi Plan (Project ID: TÁMOP-4.2.1/B-09/1/KMR-2010-0002).

Notes

^aDetermined by LC-MS.

^aDetermined by LC-MS.

^aDetermined by LC-MS.