An efficient solution phase synthesis of triazadibenzoazulenones: 'designer isonitrile free' methodology enabled by microwaves

被引：41

作者：

Hulme, Christopher ^{[1
]}

Chappeta, Shashi ^{[1
]}

Griffith, Chris ^{[1
]}

Lee, Yeon-Sun ^{[1
]}

Dietrich, Justin ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 17期

关键词：

BIOAVAILABLE OXYTOCIN ANTAGONISTS; ARMSTRONGS CONVERTIBLE ISONITRILE; BOC/CYCLIZATION UDC STRATEGY; MULTICOMPONENT UGI REACTION; AMINO ACID-DERIVATIVES; CCR5; ANTAGONISTS; DRUG DISCOVERY; ALPHA-AMINO; POTENT; 2,5-DIKETOPIPERAZINES;

D O I：

10.1016/j.tetlet.2009.02.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel two-step solution phase protocol for the synthesis of arrays of triazadibenzoazulenones is reported. The methodology employs the Ugi reaction to assemble desired diversity and acid treatment enables two tandem ring closing transformations. The order of ring closure is shown to be key for optimal conversion to the desired tetra-cyclic product and initially proceeds through a benzimidazole intermediate, followed by second ring closure to give the desired fused benzodiazepine. The two-step protocol is further facilitated by microwave irradiation. Prudent selection of the isonitrile reagent enables the correct order of ring forming events. As such the methodology represents the first example of a post-condensation Ugi modification that employs two internal amino nucleophiles. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1939 / 1942

页数：4

共 55 条

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