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

被引：6

作者：

Cao, Liming

Maciejewski, John P.

Elzner, Stephan

Amantini, David

Wipf, Peter ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 30期

基金：

美国国家卫生研究院;

关键词：

AZA-WITTIG REACTION; VIRIDIN; FURANOSTEROIDS; XESTOSPONGIA; DERIVATIVES; WORTMANNIN; THIAZOLINE; INHIBITOR;

D O I：

10.1039/c2ob25353d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5811 / 5814

页数：4

共 25 条

[1] Organic azides:: An exploding diversity of a unique class of compounds
Bräse, S
Gil, C
Knepper, K
Zimmermann, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
[2] THE THIAZOLINE RING AS A PROTECTIVE GROUP OF 2-AMINO-2-DEOXY-3-THIO-MANNOSE
BROSSMER, R
MACK, H
[J]. TETRAHEDRON LETTERS, 1981, 22 (10) : 933 - 936
[3] Synthesis of the apratoxin 2,4-disubstituted thiazoline via an intramolecular aza-Wittig reaction
Chen, JH
Forsyth, CJ
[J]. ORGANIC LETTERS, 2003, 5 (08) : 1281 - 1283
[4] A Cascade Approach to Pyridines from 2-Azido-2,4-dienoates and α-Diazocarbonyl Compounds
Chen, Zheng-Bo
Hong, Deng
Wang, Yan-Guang
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) : 903 - 905
[5] Recent progress in the synthesis of heterocyclic natural products by the Staudinger/intramolecular aza-Wittig reaction
Eguchi, S
[J]. ARKIVOC, 2005, : 98 - 119
[6] The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin
Findlay, Alison D.
Gebert, Antje
Cade, Ian A.
Banwell, Martin G.
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (09) : 1173 - 1180
[7] THE VIRIDIN FAMILY OF STEROIDAL ANTIBIOTICS
HANSON, JR
[J]. NATURAL PRODUCT REPORTS, 1995, 12 (04) : 381 - 384
[8] Ihle NT, 2004, MOL CANCER THER, V3, P763
[9] OZONOLYSIS OF OLEFINS .7. BROMOACETALDEHYDE AND IODOACETALDEHYDE BY OZONOLYSIS OF ALLYL BROMIDE AND ALLYL IODIDE
JACHAK, M
MITTELBACH, M
JUNEK, H
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (04) : 469 - 473
[10] APPLICATION OF THE INTRAMOLECULAR AZA-WITTIG REACTION TO THE SYNTHESIS OF VINYLOGOUS URETHANES AND AMIDES
LAMBERT, PH
VAULTIER, M
CARRIE, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) : 5352 - 5356

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