» Articles » PMID: 22473572

Synthesis of 1,2,4-triazines and the Triazinoisoquinolinedione DEF Ring System of Noelaquinone

Overview
Journal Org Biomol Chem
Specialties Biochemistry
Chemistry
Date 2012 Apr 5
PMID 22473572
Authors
Affiliations
Soon will be listed here.
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.

References
1.
Yip S, Cheung H, Zhou Z, Kwong F . Room-temperature copper-catalyzed alpha-arylation of malonates. Org Lett. 2007; 9(17):3469-72. DOI: 10.1021/ol701473p. View

2.
Brase S, Gil C, Knepper K, Zimmermann V . Organic azides: an exploding diversity of a unique class of compounds. Angew Chem Int Ed Engl. 2005; 44(33):5188-240. DOI: 10.1002/anie.200400657. View

3.
Xie X, Cai G, Ma D . CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds. Org Lett. 2005; 7(21):4693-5. DOI: 10.1021/ol0518838. View

4.
Ihle N, Williams R, Chow S, Chew W, Berggren M, Paine-Murrieta G . Molecular pharmacology and antitumor activity of PX-866, a novel inhibitor of phosphoinositide-3-kinase signaling. Mol Cancer Ther. 2004; 3(7):763-72. View

5.
Lang Y, Souza F, Xu X, Taylor N, Assoud A, Rodrigo R . Pentacyclic furanosteroids: the synthesis of potential kinase inhibitors related to viridin and wortmannolone. J Org Chem. 2009; 74(15):5429-39. DOI: 10.1021/jo900922q. View