Nouvelle methode de synthese de tetrahydro-2,3,4,5 benzo (b) 1H-azepines substituees en position -2 |
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Authors: | G Adam J Andrieux M Plat |
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Institution: | Laboratoire de Pharmacie Chimique II, E.R.A. 317, Faculté de Pharmacie, Université de PARIS-SUD, 11, rue Jean Baptiste Clément, 92290 Chatenay-Malabry, France |
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Abstract: | Treatment of tertiary alcohols and trisubstituted olefins of the tetrahydronaphthalene series with the HN3H2SO4 reagent leads directly and with good yields to a new class of compounds: the 3,4-dihydro 5H benzo (b) azepins substituted on position -2. The latter, on reduction, give the corresponding 2,3,4,5-tetrahydro 1H benzo (b) azepins, most of them being unknown in the literature. This work shows the high regiospecificity of this ring expansion reaction which can be explained by electronic and steric effects. |
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