Anderson, JC;
Noble, A;
Torres, PR;
(2012)
An intramolecular nitro-Mannich route to functionalised tetrahydroquinolines.
TETRAHEDRON LETTERS
, 53
(42)
5707 - 5710.
10.1016/j.tetlet.2012.08.062.
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Abstract
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.
| Type: | Article |
|---|---|
| Title: | An intramolecular nitro-Mannich route to functionalised tetrahydroquinolines |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1016/j.tetlet.2012.08.062 |
| Publisher version: | http://dx.doi.org/10.1016/j.tetlet.2012.08.062 |
| Language: | English |
| Additional information: | This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY), which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. |
| Keywords: | Nitro-Mannich, Tetrahydroquinoline, Diastereoselective, Cyclisation, Heterocycle |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/1372289 |
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