A library of symmetrical and unsymmetrical bis-(β-aminoamides) has been prepared starting from symmetrical secondary diamines by using a double Ugi four-component reaction. A sacrifical Mumm rearrangement, thanks to the use of 2-hydroxymethyl benzoic acid, is necessary to suppress the competing split-Ugi reaction, increasing the yield and simplifying the purification step. The scope, the reaction conditions, and the role of water in trapping the nitrilium intermediate are also discussed.
International audienceThe interaction of isocyanides with acyl chlorides was first reported by Nef in 1892. The resulting α-keto imidoyl chlorides may be hydrolyzed to form α-keto amides. Relatively few data are available on this reaction and the chemistry of α-keto imidoyl chlorides has been largely underestimated until some recent uses in intra- and intermolecular couplings with a variety of nucleophiles. The present review brings a comprehensive presentation of the Nef reaction of isocyanides focusing on mechanism and regioselectivity issues
Synthesis of Heteroarylogous 1H-Indole-3-carboxamidines via a Three-Component Interrupted Ugi Reaction. -The novel one-pot multicomponent reaction is based on the reaction of N-alkyl-N-(1H-indol-2-ylmethyl)amines, with various carbonyl compounds, such as aldehydes including formaldehyde or cyclohexenone, and variously functionalized isocyanides. -(LA SPISA, F.; MENEGHETTI, F.; POZZI, B.; TRON*, G. C.; Synthesis 47 (2015) 4, 489-496, http://dx.doi.org/10.1055/s-0034-1378921 ; Dip. Sci. Farm., Univ. Studi Piemonte
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