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Paper | Special issue | Vol 74, No. 1, 2007, pp.293-307
Published online, 27th July, 2007
DOI: 10.3987/COM-07-S(W)6
Synthesis and Transformation of N,N-Dimethylaminomethylidene Derivatives of Indolylglycines and Some Other Dipeptides

Renata Jakse, Ljubo Golic, Anton Meden, Uros Groselj, Jurij Svete,* and Branko Stanovnik*

*Department of Organic Chemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SI-1000 Ljubljana, Slovenia

Abstract

Indolyl glycinates (3, 7, and 11) were transformed with t-butoxybis(dimethylamino)methane (Bredereck’s reagent) into 3-[(dimethylamino)methylidene]-2,3-dihydropyrazino[1,2-a]indole-1,4-dione (4), 3-(dimethylamino)-2-[(1H-indol-3-ylcarbonyl)amino]propenoate (8), and 2-(1-methyl-1H-indol-2-yl)-1,3-oxazol-5(4H)-one derivative (12). Dipeptides (16a-c) were transformed with Bredereck’s reagent into the hydantoin (imidazolidine-2,4-dione) derivatives (17a-c).