Efficient synthesis of fumaric amides through cross-metathesis of acrylic amides with the NHC Grubbs ruthenium catalyst

Transition metals in organic synthesis: Highlights for the year 2005

“…(224)) [1210]. Homo-alkene-alkene CM of was described [1211,1212]. (224) Ruthenium catalyzed alkene-alkene CM of styrenes [1213], 1-allyl-tetrahydro-␤-carboline and -tetrahydroquinoline [1214], propenoic esters [1215,1216], alkenylsilanes [283,1217], allyl trimethylsilane [1218], conjugated dienes [1219,1220], allyl cyanide [1221], acrylonitrile [1222], ethenylazulene [1223], N-allylpyrimidines [1224], terminal 1-en-4-ols [644] and ␤-hydroxyenones [1225] with terminal alkenes were described.…”

Synthesis of Small Tripeptide Molecules through a Catalysis Sequence Comprising Metathesis and Aminohydroxylation

“…Other examples led to incomplete yields after a reaction time of 10 h with the remaining starting material in the range of 8–15 % as estimated from the 1 H NMR spectra of the crude material (Table 1, entries 4, 5 and 35 % in the formation of product 3 f from β‐alanine incorporation). In these cases, analytically pure products 3 d – f were obtained directly through crystallization from the reaction mixture or after column chromatography 12. Importantly, all products were obtained as pure fumaric amides, that is, with complete E selectivity with regard to the newly established CC double bond.…”

Synthesis and Antifungal Studies of (2E)‐N‐Benzyl‐N′‐phenylbut‐2‐enediamide and (2E)‐N,N′‐Dibenzylbut‐2‐enediamide Analogues

“…Compounds 3a and 3i were synthesised previously [22,23]; however NMR data for 3a are not reported in Bi et al [22] and are therefore presented below. The 1 H and 13 C NMR data for 3i (32% yield) was consistent with that reported in Streuff and Muñiz [23]. Antifungal Susceptibility Test.…”

“…Some of the synthetic approaches to synthesising these amides include the Aza-Michael addition of an amine to N-phenylmaleimide using trans-N,N,N ,N -tetramethylcyclohexanediamine (TMCDA) as a receptor [22], crossmetathesis of acrylic amide with NHC Grubbs ruthenium catalyst [23], and the use of DCC, either with 1-hydroxybenzotriazole (HOBT) or but-2-en-1,4-dioic acid and benzylamine [24], which we have chosen to adopt with some modification along with the modified method of esterification of carboxylic acids, in which we have formed amides rather than the esters by using amines instead of alcohols [25].…”

“…To the best of our knowledge, no biological studies of these compounds have been reported and only the syntheses of 3a [22] and 3i [23] have been reported. We present here the synthesis of several butanediamine analogues with different electron donating and withdrawing groups (OCH 3 , NO 2 , Cl, F) and explored their potential to act as antifungal agents.…”