An intramolecular nitro-Mannich route to functionalised tetrahydroquinolines

TETRAHEDRON LETTERS

卷:53

Article

Anderson, James C.¹  Noble, Adam¹  Torres, Pascual Ribelles¹ 

[1] UCL, Dept Chem, London WC1H 0AJ, England

关键词: Nitro-Mannich;    Tetrahydroquinoline;    Diastereoselective;    Cyclisation;    Heterocycle;   

DOI  :  10.1016/j.tetlet.2012.08.062

来源: Elsevier

【 摘 要 】

A simple protocol for the diastereoselective synthesis of 3-nitrotetrahydroquinolines has been developed using an intramolecular nitro-Mannich reaction. In situ formation of an imine generated from treatment of 2-(2-nitroethyl)phenylamine with an aldehyde, in EtOH at room temperature, and subsequent addition of NH4OH, led to the formation of trans-products in high yield and diastereoselectivity for 15 representative examples. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.

【 授权许可】

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