Expeditious synthesis of C2- or N4-aryl-1,4-benzothiazin-3-one via orthogonal Pd-catalyzed C-arylation and Cu-catalyzed N-arylation

被引：3

作者：

Huang, Wei-Sheng ^{[1
]}

Xu, Rongsong ^{[1
]}

Dodd, Rory ^{[1
]}

Shakespeare, William C. ^{[1
]}

机构：

[1] ARIAD Pharmaceut Inc, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 02期

关键词：

C-arylation; N-arylation; Pd-catalysis; Cu-catalysis; 1,4-Benzothiazin-3-one; Heterocycle synthesis; ARYL HALIDES; ALPHA-ARYLATION; INHIBITORS; OXINDOLES; AMIDES; DERIVATIVES; POTENT; CARBOXAMIDES; EQUIVALENTS; CONVENIENT;

D O I：

10.1016/j.tetlet.2013.11.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct, chemo-specific arylation at C-2 or N-4 of 1,4-benzothiazin-3-one with aryl halides, based on Pd or Cu catalyst system, respectively, provided easy entry to arylated derivatives, a class of molecules not easily accessible via existing methods. Under Pd-catalysis conditions with LiHMDS as the base, N-arylation of 1,4-benzothiazin-3-one was inhibited leading to C alpha-arylation of a secondary amide without the need for protection and de-protection of more acidic amido NH. (C) 2013 Elsevier Ltd. All rights reserved.

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页码：441 / 444

页数：4

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