Quinoline derivatives represent an important class of heterocycles. The quinoline ring system occurs in various natural products, especially in alkaloids such as quinine for the treatment of malaria and thereafter in many synthetic pharmaceutical agents such as chloroquine and mefloquine. In addition, the quinoline skeleton is often used for the design of many ligands and functional material. Among the quinoline derivatives, 6-hydroxyquinoline is a starting heterocycle for pharmaceutical research and electronic material. Unfortunately, quinoline derivatives were obtained using toxic reagents like arsenic(V) oxide in sulfuric acid as solvent… From the view point of green chemistry, the toxic reagents like arsenic(V) oxide was removed, water was used as green solvent and alternative microwave irradiations were developed. Our optimization furnished one efficient domino reaction with a “one pot eleven steps” using only glycerol, nitrobenzene instead 4-hydroxyaniline, sulphuric acid and water via modified Skraup reaction and Bamberger rearrangement. This process permitted: (i) the reduction of nitrobenzene to 4-hydroxyaniline via the successive formation of N-hydroxylaniline and aromatic nucleophilic substitution by elimination–addition; (ii) the double dehydratation of glycerol to acrolein; and (iii) the addition of 4-hydroxyaniline to acrolein. To the best of our knowledge, this is the first time that the 6-hydroxyquinoline has been obtained under such green conditions.[1] [1] H. Saggadi, D. Luart, N. Thiebault, I. Polaert, L. Estel, C. Len, Catal. Commun. 2014, 44, 15.

Synthesis of 6-hydroxyquinoline starting from glycerol via improved microwave-assisted modified Skraup reaction and Bamberger rearrangement

249th National Meeting (2015)

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