Abstract
The scope of 1,3,5-triazine inverse electron-demand Diels-Alder
(IDA) reactions was expanded to include 2-aminoindoles as productive
dienophiles leading to various 3-aza-α-carbolines in excellent
yields. Furthermore, the two ester groups of the IDA product were
differentiated via reduction of the C4-ester to its corresponding
alcohol. This new IDA reaction could be potentially applied to the
synthesis of various 3-aza-mescengrincin analogues that may possess
neuroprotective activities.
Key words
2-aminoindoles - inverse electron-demand Diels-Alder reactions - heterocycles - 3-aza-α-carbolines - regiospecific
syntheses
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