2'-Deoxy-2'-N-phthaloyl nucleosides were prepared from arabino nucleosides by triflate displacement with phthalimide in the presence of DBU. The corresponding phosphoramidites suitable for automated oligonucleotide synthesis were also synthesized. The scalability of described procedures was demonstrated on a 100-g scale preparation of 2'-deoxy-2'-amino-C phosphoramidite.

Treatment of 3-hydroxyoxindoles with trichloroacetonitrile (1.3 equiv.) and a catalytic amount of DBU (0.1 equiv.) followed by addition of nucleophiles (1.5 equiv.) and diphenylphosphoric acid (0.2 equiv.) afforded the 3,3-disubstituted oxindoles in good to excellent yields. DFT computations supported the notion that the reaction went through the 1-alkyl-2-oxo-2H-indol-1-ium intermediate.

A novel DBU-mediated oxidative cyanation of α-amino carbonyl compounds by using air as the sole oxidant was developed under mild metal-free conditions for the first time. The reaction involves a tandem oxidation/Strecker reaction/oxidation process and provides a new and efficient method for the construction of α-iminonitriles in good to high yields in a single step.

1,1-Cyclopropane aminoketones were efficiently synthesized in high yields by the tandem reaction of α-amino aryl ketones with vinyl sulfonium salts using DBU as the base in CH(2)Cl(2). This methodology was utilized to synthesize 2-benzoyl quinolines.

Evaluation of a new proton sponge, bis-1,1,8,8-(tetramethylguanidino)naphtalene (TMGN), in substituted phenols O-alkylation by methyl iodide in DMF has been studied. Kinetic measurements were performed in N,N-dimethylformamide-d7 and followed by H NMR using stoichiometric amounts of reagents. Plot of the results shows that the reaction follows an almost perfect second order rate law. However th...

Alkylation of 5-nitroindol-4-ylacetonitriles with ethyl chloroacetate, α-halomethyl ketones, and chloroacetonitrile followed by a treatment of the products with chlorotrimethylsilane in the presence of DBU gives 1-cyanopyrrolo[3,2-e]indoles substituted in position 2 with electron-withdrawing groups.

Thymine residues in an oligodeoxyribonucleotide are subject to methylation at N3 by the internucleotide methyl phosphotriester linkages. This alkylation occurs most rapidly in the presence of a strong base such as DBU, but also takes place, at a much slower rate, during oligonucleotide synthesis.

The combination of a catalytic amount of Cu(OTf)2 and less than a stoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under an O2 atmosphere effectively promoted the N-nitrosation of both secondary aromatic/aliphatic amines and tertiary aromatic amines with nitromethane (CH3NO2) leading to the preparation of N-nitrosamine derivatives.

Activated by DBU, N-haloimides can be used as both halogen and nitrogen sources to achieve the difunctionalization of terminal alkynes, giving rise to useful halogenated enamines with high efficiency and high regio- and stereoselectivities. The cascade reaction features simple manipulation, mild conditions, a broad substrate scope, readily available reagents, and atom-economy.

Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σH-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields.