Methanol reacts with aminoarenes in the presence of a catalytic amount of ruthenium trichloride hydrate combined with tributylphosphite at 180 °C to give the corresponding N-methylaminoarenes in high yields.

Ruthenium complex shows high catalytic activity for the reaction of 2-aminophenol with primary alcohols to give the corresponding 2-substituted benzoxazoles in high yields. Similarly, 2-substituted benzimidazoles are also synthesized readily by the ruthenium catalyzed reaction of 1,2-phenylenediamine with primary alcohols.

2-Butyne-1,4-diol reacts with aliphatic amines in the presence of a catalytic amount of [RuCl2(PPh3)3] at 150 °C to give N-alkylpyrroles in good yields. 1,4-Butanediol reacts with aromatic or aliphatic amines to give N-substituted pyrrolidines in excellent yields; [RuCl2(PPh3)3] and [RuCl3·nH2O–3PBu3] are the best catalysts for aromatic and aliphatic amines, respectively. The reaction of 2-butene-1,4-diol with alkyl amines gives a 1:1 mixture of N-substituted pyrroles and pyrrolidines in high yield.

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