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Pure Appl. Chem., 2007, Vol. 79, No. 11, pp. 1869-1877

Distillable ionic liquids for a new multicomponent reaction

Anthony E. Rosamilia1, Christopher R. Strauss2 and Janet L. Scott1

1 Centre for Green Chemistry, Monash University, Wellington Road, Clayton, Victoria 3800, Australia
2 Strauss Consulting Pty Ltd., P.O. Box 1065, Kunyung LPO, Mt. Eliza, Victoria, Australia

Abstract: Adducts of dimethylamine and carbon dioxide form a "distillable ionic liquid" (DIMCARB) that may used as both a reaction medium and catalyst in the direct, atom-economical synthesis of useful synthetic building blocks, such as mono-condensed α,β-unsaturated ketones. The utilization of such building blocks in the synthesis of two new classes of versatile macrocycles, by a sequence of condensation reactions (H2O by-product), is described. Investigation into the mechanism of action of DIMCARB catalysis and observation of an aniline impurity arising from a competing reaction sequence led to development of a new multicomponent reaction for the direct preparation of 2- or 4-substituted anilines. Some of the macrocycles and anilines are, respectively, supramolecular host compounds and ligands for the preparation of metal complexes.