Abstract
A series of novel N-acyl cyclic urea derivatives (3a-3l) have been synthesized by the reactions of 1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one (1) with various acyl chlorides in the yields of 35-95%. Subsequently, N-acyl cyclic urea derivatives containing α-tertiary amine (5a-5k) have been synthesized by the nucleophilic substitution reaction of 1-(2-haloacetyl)-3-((6chloropyridin-3-yl)methyl)imidazolidin-2-one (3e or 3f) with various secondary amines in the yields of 49-86%. The synthesized compounds were characterized by 1 H NMR spectroscopy, 13 C NMR spectroscopy, high-resolution mass spectroscopy, IR and elemental analysis.
Highlights
The cyclic urea derivatives have been reported to display a wide range of biological activities, such as the HIV protease inhibitors,[1] selective NK1 antagonists,[2] Chk[1] inhibitors,[3] calciumselective fluoroionophore,[4] anti-Alzheimer’s disease[5] and herbicide.[6]
To prepare molecules having both N-acyl cyclic urea and Nheterocycles would be a worthwhile programme. These compounds have polyfunctional groups and maybe exhibit multidirectional activity. Based on these facts and in continuation of research on the application of 1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one (1),[22] here we report the synthesis of novel N-acyl cyclic urea derivatives
Acylation of 1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one (1) In order to optimize the reaction conditions of N-acylation, we investigated the effects of solvents, times and bases on the reaction of 1 with benzoyl chloride (2g) (Table 1)
Summary
The cyclic urea derivatives have been reported to display a wide range of biological activities, such as the HIV protease inhibitors,[1] selective NK1 antagonists,[2] Chk[1] inhibitors,[3] calciumselective fluoroionophore,[4] anti-Alzheimer’s disease[5] and herbicide.[6]. Increasing the temperature from 70 oC to 110 oC could dramatically increase the yield of 1benzoyl-3-((6-chloropyridin-3-yl)methyl)imidazolidin-2-one (3g) in shorter reaction time. The reactions of 1 with various aliphatic acyl chlorides gave N-acyl cyclic urea derivatives 3a-f in excellent yields of 84-95% (entries 1-6).
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