Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ
Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ
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DOI：
10.1016/j.tetlet.2008.12.101
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发表时间：
2009-03-18
影响因子：
1.8
通讯作者：
Todd, Matthew H.
中科院分区：
文献类型：
--
作者：
Tsang, Althea S. -K.;Todd, Matthew H.
The oxidation of N-phenyltetrahydroisoquinolines occurs rapidly with DDQ. Under ambient conditions and in the presence of nitromethane, the corresponding beta-nitroamine derivatives are isolated in good to excellent yields. Variation in the electronic nature of the isoquinoline and the N-phenyl substituent showed that a broad range of substituents are tolerated, with electronic communication between the isocluinoline aromatic ring and the C1 carbon being stronger than with the N-aryl ring. Reduction of the beta-nitroamines to the corresponding novel chiral vicinal diamines are straightforward, Examination of the reaction by H-1 NMR spectroscopy suggested that the reaction proceeds via an iminium ion, which then reacts with nitromethane upon work-up. This information was used to shorten the required reaction time. (C) 2009 Elsevier Ltd. All rights reserved.
