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DOI: 10.1055/s-0029-1218345
Regiospecific Syntheses of 3-Aza-α-carbolines via Inverse Electron-Demand Diels-Alder Reactions of 2-Aminoindoles with 1,3,5-Triazines
Publikationsverlauf
Publikationsdatum:
03. November 2009 (online)
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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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- Supporting Information
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References and Notes
HOMO energies for indole and 8a are -124.5 kcal/mol and -114.1 kcal/mol, respectively (calculated using Spartan with the B3LYP/6-31G* method).
24HOMO energies for 8a, 8b, and 8c are -114.1, -113.2, and -113.9 kcal/mol, respectively (to simplify the calculation, the free base forms were used, using Spartan with the B3LYP/6-31G* method).
27CCDC 748786 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.