期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 7, 期 5, 页码 986-995出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b819610a
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The bromination of a series of cyclohexenyl substituted secondary amines 1a-i has been investigated using Br-2, PHT and NBS. In the case of Br-2 and NBS the secondary amines preferentially undergo N-bromination. In contrast, PHT cleanly affords the products of alkene dibromination. In the case of Br-2 the N-bromo species then give the products of alkene dibromination, albeit less efficiently. On subsequent treatment with K2CO3 these dibromides form the corresponding hexahydroindoles 2a-h and octahydroquinoline 2i. The presence of an N-substituent bearing a stereogenic centre (1h and 1i) was studied and the products 2h and 2i were isolated with no diastereoselectivity. When NBS was used a novel cyclisation, forming bromo-substituted octahydroindoles 9a, b and d, was observed. In relation to this sequence it was shown that these products were not intermediates in the former Br-2/PHT processes and that the reaction only proceeded in the presence of the succinimide by-product of N-bromination.
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