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

doi:10.1039/C2OB25353D

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Organic & Biomolecular Chemistry

Issue 30, 2012

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

Liming Cao,^a John P. Maciejewski,^a Stephan Elzner,^a David Amantini^a and Peter Wipf*^a

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Department of Chemistry and Center for Chemical Methodologies and Library Development, 219 Parkman Avenue, 15260 Pittsburgh, USA
E-mail: pwipf@pitt.edu;
Fax: +1 412 624 0787 ;
Tel: +1 412 624 8606

Org. Biomol. Chem., 2012,10, 5811-5814

DOI: 10.1039/C2OB25353D
Received 20 Feb 2012, Accepted 19 Mar 2012
First published online 20 Mar 2012

This article is part of themed collection: Organic & Biomolecular Chemistry 10th Anniversary

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Abstract
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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.