Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring system of noelaquinone†‡§,10.1039/C2OB25353D

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

Liming Cao,John P. Maciejewski,Stephan Elzner,David Amantini,Peter Wipf

Organic & Biomolecular Chemistry Pub Date : 03/20/2012 00:00:00 , DOI:10.1039/C2OB25353D

Abstract

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.