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Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold
Institute for Molecules and Materials, Radboud University Nijmegen, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands
MSD Research Laboratories, P.O. Box 20, 5340 BH Oss, The Netherlands
Solvay Pharmaceuticals, Sector Discovery Weesp, P.O. Box 900, 1380 DA Weesp, The Netherlands
* Author to whom correspondence should be addressed.
Received: 5 February 2010; in revised form: 26 March 2010 / Accepted: 30 March 2010 / Published: 30 March 2010
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
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MDPI and ACS Style
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.
Blanco-Ania D, Valderas-Cortina C, Hermkens PH, Sliedregt LA, Scheeren HW, Rutjes FP. Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold. Molecules. 2010; 15(4):2269-2301.
Blanco-Ania, Daniel; Valderas-Cortina, Carolina; Hermkens, Pedro H.H.; Sliedregt, Leo A.J.M.; Scheeren, Hans W.; Rutjes, Floris P.J.T. 2010. "Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold." Molecules 15, no. 4: 2269-2301.