AI Article Synopsis
- - A new method is introduced for efficiently synthesizing complex 1,2,3,4-tetrahydroquinoxalines with high diastereoselectivity, using commercially available starting materials. - The synthesis involves a key nitro-Mannich reaction followed by sequential reduction and Pd-catalyzed reactions, resulting in pure β-nitro amines and highly substituted products. - The use of methanesulfonic acid enhances the reaction with non-basic imines, making this 3-step process valuable for creating drug-like compounds.
Article 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.
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| http://dx.doi.org/10.1039/c6ob01530a | DOI Listing |
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