FLUOROUS SYNTHESIS - FLUOROUS PROTOCOLS FOR THE UGI AND BIGINELLI MULTICOMPONENT CONDENSATIONS

Citation
A. Studer et al., FLUOROUS SYNTHESIS - FLUOROUS PROTOCOLS FOR THE UGI AND BIGINELLI MULTICOMPONENT CONDENSATIONS, Journal of organic chemistry, 62(9), 1997, pp. 2917-2924
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
00223263
Volume
62
Issue
9
Year of publication
1997
Pages
2917 - 2924
Database
ISI
SICI code
0022-3263(1997)62:9<2917:FS-FPF>2.0.ZU;2-4
Abstract
A new protocol for multicomponent condensation reactions that uses flu orous (highly fluorinated) substrates is introduced. This method takes advantage of the ease of purification of fluorous compounds by liquid -liquid extractions between fluorous and organic solvents. The applica tion of this method to the Ugi and Biginelli reactions is described. T he condensation products of these two reactions, amino acid amides and dihydropyrimidines, are easily obtained without chromatography in hig h purities, even though the other reagents are used in very large exce sses. This is. the first demonstration of the suitability of fluorous phase methods for combinatorial synthesis of ''druglike'' organic mole cules.