Brian P. Jones

DBU Catalysis of N,N′-Carbonyldiimidazole-Mediated Amidations§

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) has been found to catalyze the amidation of acyl imidazoles. The rate acceleration is especially evident with traditionally unreactive, electron-deficient anilines. DBU is readily available and offers safety and cost advantages over more commonly employed catalysts such as 1-hydroxybenzotriazole.

Inhibitors of MMP-1: an examination of P1′ Cα gem-disubstitution in the N-carboxyalkylamine and glutaramide carboxylate series

Abstract Modification of the N-carboxyalkylamine 3 by independent replacement of the P1′ NH group for CH2 and introduction of P1′ gem-cyclohexyl substitution affords compounds 5 and 6a which retain appreciable activity against MMP-1 (IC50s = 0.023 μM and 0.09 μM, respectively). The glutaramide 7a which incorporates both these structural changes also retains potent activity (IC50 = 0.038 μM).

TANDEM CARBOLITHIATION/CYCLIZATION OF 2-(3-PHENYL-2-PROPEN-1-YL) OXAZOLINES. A NOVEL ROUTE TO CYCLOBUTANE DERIVATIVES

Abstract Reaction of the 2-(3-phenyl-2-propen-1-yl) oxazolines 1 and 3 with organolithium reagents leads to cyclobutane ring formation by a novel tandem carbolithiation/cyclization sequence. The products (e.g., 2a and 4a) may be hydrolyzed to the corresponding substituted cyclobutanones (e.g., 7 and 8).