The synthesis of 5-aminoindane derivates

Some of the five-membered ring substituted indan derivatives show very important biological activities. For example, cis-1S,2R-aminoindanol is a component of the inhibitor of protease in the human immunodeficiency virus (HIV). Enantiomerically pure aminoindanol derivatives have recently been described as highly efficient ligands in the titanium-catalysed asymmetric Diels-Alder reaction. Furthermore, a series of optically active aminoindanol derivatives was used in the catalytic enantioselective addition of diethylzinc to aldehyds. Bromination of hydroaromatic compounds is an important transformation, as the resulting brominated products are versatile intermediates in organic synthesis.In this work, we investigated bromination reactions of 5-aminoindan (1) and 5-acetoaminoindan (2) using different reaction conditions to synthesize brominated derivatives. We prepared a variety of brominated derivatives (93, 94, 95, 96, 97, 98, 99,100, 104, 105, 106) and accomplished the first, quantitative and highly regioselective synthesis of all brominated derivatives. The structures of all compounds have been elucidated on the basis of 1H and 13C NMR spectral data by comparison of some spectral data of related systems reported in the literature.