Four‐Component Cyclocondensation of Aminodiazines, Glyoxal, Formaldehyde, and Methanol to Imidazolidines

Abstract

Four‐component reaction of aminodiazines (2‐aminopyrimidine and 2‐aminopyrazine), glyoxal, formaldehyde, and methanol yields trans‐4,5‐dimetoxy‐1,3‐bis(2‐pyrimidinyl)imidazolidine (5a) and trans‐4,5‐dimetoxy‐1,3‐bis(2‐pyrazinyl)imidazolidine (5b), respectively. Changing methanol to acetonitrile leads to the formation of the corresponding 1,3‐bis(2‐pyrimidinyl) and‐1,3‐bis(2‐pyrazinyl)‐ derivatives of trans‐4,5‐dihydroxyimidazolidine (6). Details of the proposed mechanism are discussed.

Keywords:

• 2‐aminopyrazine
• 2‐aminopyrimidine
• formaldehyde
• glyoxal
• imidazolidine

Acknowledgment

The authors thank the Research Council of the University of Tehran for financial support.