Imidazo[1,2-a]pyridine,Imidazo[1,2-a]pyrimidine and Imidazo[1,2-a]pyrazine are important building blocks, used in medicinal chemistry.

Synthesis of Imidazo[1,2-a]pyridine.

1.

 

 

To a solution of the appropriately substituted 2-aminopyridine (0.08 mole) in 95% ethanol or dioxane (30-50 mL),was added an equimolar amount of the required a-halo ketone or a-haloaldehyde . After the addition of 2 mole equiv. of NaHCO3, the stirred mixture was refluxed for 14-22 hr. The dark brown reaction mixture was then filtered and the filtrate was made basic (pH 10) with 5% aqueous NaOH. The aqueous solution was extracted with three 100 mL portions of CHCl3 and the combined extracts were dried (anhydrous Na2CO3) and filtered. The CHCl3 was then removed in vacuo and the residual oil was vacuum distilled to yield the substituted imidazo[l,2-a]pyridine.

 

2.

 

2-amino pyrimidine (0.5 mol) was dissolved in 50% hydro-alcoholic solution in presence of sodium hydrogenocarbonate (0.6 mol). To this mixture, a water solution (40%) of chloroacetaldehyde (1 mol) was added slowly under nitrogen with vigorous stirring and was refluxed for 48 h. After this period, the reaction mixture was cooled, concentration in vacua, poured into water and extracted with hot chloroform. The organic layer was dried (MgSO4) and evauorated in vacuo. Pure imidazo[1.2-a]pyrimidine was obtained after chromatography on a silica gel column (eluent :ethylacetate).

 

3.

 

A solution of 2.85 g (30.0 mmol) of aminopyrazine in 100 mL of CH2Cl2 was added to 28.5 g alumina . The resulting stirred suspension was treated with a solution of 2,3-epoxypropanal (cis and trans; 2.58 g, 30.0 mmol) in 10 mL of CH2Cl2 and the suspension was stirred overnight at room temperature under N2. The mixture was vacuum filtered, and the cake was washed with 100 mL of CH2Cl2 and two, 100-mL portions of 2% MeOH-CH2Cl2. The combined filtrate was concentrated under vacuum at 25 oC to give 3.6 g of orange solid, which was chromatographed on activity III alumina. Elution with CHzCl2 gave fractions containing 1.25 g of pure 3-(l-hydroxyethyl)- imidazo[l,2-a]pyrazine (26%).

The application of Imidazo[1,2-a]pyridine.

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