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Molecules 2010, 15(4), 2269-2301; doi:10.3390/molecules15042269
Article

Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold

1, 1, 2, 3, 1 and 1,*
Received: 5 February 2010 / Revised: 26 March 2010 / Accepted: 30 March 2010 / Published: 30 March 2010
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Abstract

The synthesis of a small library of dihydrouracils spiro-fused to pyrrolidines is described. These compounds are synthesized from b-aryl pyrrolidines, providing products with the 2-arylethyl amine moiety, a structural feature often encountered in compounds active in the central nervous system. The b-aryl pyrrolidines are synthesized through a three-step methodology that includes a Knoevenagel condensation reaction, a 1,3-dipolar cycloaddition reaction, and a nitrile reduction.
Keywords: Knoevenagel condensation; 1,3-dipolar cycloaddition; azomethine ylide; parallel synthesis; spiro dihydrouracils Knoevenagel condensation; 1,3-dipolar cycloaddition; azomethine ylide; parallel synthesis; spiro dihydrouracils
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Blanco-Ania, D.; Valderas-Cortina, C.; Hermkens, P.H.; Sliedregt, L.A.; Scheeren, H.W.; Rutjes, F.P. Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold. Molecules 2010, 15, 2269-2301.

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