Anderson, JC;
Campbell, IB;
Campos, S;
Reid, IH;
Rundell, CD;
Shannon, J;
Tizzard, GJ;
(2016)
Reductive conjugate addition nitro-Mannich route for the stereoselective synthesis of 1,2,3,4-tetrahydroquinoxalines.
Organic & Biomolecular Chemistry
, 14
(35)
pp. 8270-8277.
10.1039/c6ob01530a.
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Abstract
A concise, high yielding and structurally divergent synthesis of complex 1,2,3,4-tetrahydroquinoxalines with excellent diastereoselectivity is described. A wide array of nitroalkenes and imines derived from commercially available aromatic aldehydes and 2-chloroanalines were subjected to a key reductive conjugate addition nitro-Mannich reaction to give diastereomerically pure β-nitro amines. Sequential reduction of the nitro function followed by Pd-catalyzed intramolecular N-arylation of the resultant primary amine onto the 2-chloroanailine gives highly substituted 1,2,3,4-tetrahydroquinoxalines. Non basic imines were found to participate better in the nitro-Mannich reaction if the stronger acid methanesulfonic acid was used to promote the reaction. The 3 step reaction sequence should be useful for the array synthesis of drug like scaffolds.
Type: | Article |
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Title: | Reductive conjugate addition nitro-Mannich route for the stereoselective synthesis of 1,2,3,4-tetrahydroquinoxalines |
Location: | England |
Open access status: | An open access version is available from UCL Discovery |
DOI: | 10.1039/c6ob01530a |
Publisher version: | http://dx.doi.org/10.1039/c6ob01530a |
Language: | English |
Additional information: | © The Royal Society of Chemistry 2016 |
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/1513254 |
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