A Novel and Efficient Reaction of Imidazolidin-2-one and N-Acylbenzotriazoles: A Facile Synthesis of 1-Acylimidazolidin-2-one

Abstract

Acylation of imidazolidin-2-one with readily available N-acylbenzotriazoles, in the presence of K₂CO₃, produced 1-acylimidazolidin-2-ones and N,N′-diacyl-imidazolidin-2-one in moderate to good yields. The utilization of N-acylbenzotriazoles which make the reaction simple and mild, may be especially advantageous when the corresponding acid chlorides are not stable or not easily prepared. It's also an example of the reaction of N-acylbenzotriazoles and amide.

Keywords:

• Acylation
• N-acylbenzotriazoles
• 1-acylimidazolidin-2-one
• amides

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (No. 20676123) and National Key Technology R&D Program (No. 2007 BAI34B06) for financial support.

Notes

^a The reactions were all carried out at 80 °C, except that entries 2, 3, 4, and 6 were at reflux temperature.

^b The mole ratio was 2: Base.

^c Isolated yield.

^a Isolated yield.

^a The reactions were all carried out at 80 °C in toluene except entries 16 and 17.

^b Isolated yield.

^c The reactions were carried out at 80 °C in toluene using K₂CO₃ as base.

^d The reactions were carried out at room temperature in THF using NaH as base.