Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone

Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone

The intramolecular Staudinger-aza-Wittig reaction is used for a general synthesis of 1,2,5,6-tetrahydro-1,2,4-triazines, a structural motif reported for the natural product noelaquinone. The DEF moiety of noelaquinone was obtained in 13 steps and 2% overall yield, and the structure of the synthetic...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-08, Vol.10 (30), p.5811-5814
Hauptverfasser: Cao, Liming, Maciejewski, John P, Elzner, Stephan, Amantini, David, Wipf, Peter
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products - chemistry
Chemistry Techniques, Synthetic
Heterocyclic Compounds, 4 or More Rings - chemistry
Isoquinolines - chemical synthesis
Isoquinolines - chemistry
Triazines - chemical synthesis
Triazines - chemistry
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Zusammenfassung:The intramolecular Staudinger-aza-Wittig reaction is used for a general synthesis of 1,2,5,6-tetrahydro-1,2,4-triazines, a structural motif reported for the natural product noelaquinone. The DEF moiety of noelaquinone was obtained in 13 steps and 2% overall yield, and the structure of the synthetic product was confirmed by X-ray analysis.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25353d