| Autor: |
Langer P; Ernst-Moritz-Arndt-Universität Greifswald Institut für Chemie und Biochemie Soldmannstrasse 16, 17487 Greifswald, Germany. peter.langer@uni-greifswald.de, Anders JT, Weisz K, Jähnchen J |
| Jazyk: |
angličtina |
| Zdroj: |
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2003 Aug 18; Vol. 9 (16), pp. 3951-64. |
| DOI: |
10.1002/chem.200204566 |
| Abstrakt: |
The sodium hydride mediated cyclization of arylacetonitriles with oxalic acid bis(imidoyl) dichlorides, aza-analogues of oxalyl chloride, afforded functionalized 2-alkylidene-3-iminoindoles with very good regio- and E/Z selectivity. Excellent chemoselectivities were observed for functionalized substrates. Based on these results a domino "cyclization-lactamization" reaction of bis(imidoyl) chlorides with methyl 2-(cyanomethyl)benzoate was developed. This process allowed a convenient one-pot synthesis of indolo[1,2-b]isoquinolin-5-ones related to tryptanthrin. A new and convenient synthesis of delta-carbolines by intramolecular electrocyclization-elimination reactions of 2-alkylidene-3-iminoindoles was developed. It was shown that delta-carbolines selectively bind to triplex or duplex DNA (intercalation). Indirubine analogues were prepared by deprotection and lactonization of functionalized 2-alkylidene-3-iminoindoles. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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