Efficient synthesis of functionalized 6-substituted-thiosalicylates via microwave-promoted Suzuki cross-coupling reaction

被引：9

作者：

Liu, Yu-Chao ^{[1
]}

Qu, Ren-Yu ^{[1
]}

Chen, Qiong ^{[1
]}

Wu, Qiong-You ^{[1
]}

Yang, Guang-Fu ^{[1
]}

机构：

[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China

来源：

TETRAHEDRON | 2014年 / 70卷 / 17期

关键词：

Pyrimidinyl(thio)salicylic acids; 6-Substituted-thiosalicylates; Suzuki cross-coupling reactions; Microwave irradiation; ASSISTED SYNTHESIS; PARALLEL SYNTHESIS; BENZOPENTATHIEPIN; HERBICIDES; TRANSFORMATION; ELLAGITANNIN; ALKALOIDS; VARACIN; DESIGN;

D O I：

10.1016/j.tet.2014.02.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Functionalized 6-substituted-thiosalicylates are key intermediates for the synthesis of pyrimidinyl(thio) salicylic acids, a group of important herbicides targeting plant acetohydroxyacid synthase. Therefore, it is of great interest to develop an efficient method for the syntheses of 6-substituted-thiosalicylates. Herein, we have developed a direct and efficient method for the synthesis of functionalized 6-substituted-thiosalicylates (4) from aryl iodide (1) by using an improved microwave-assisted Suzuki cross-coupling reaction. Almost all the reactions proceeded smoothly and afforded moderate to excellent yields of products. Moreover, this protocol is obviously superior to the traditional available methods and could be utilized to synthesize pyrimidinyl(thio)salicylic acid and its derivatives. (C)2014 Elsevier Ltd. All rights reserved.

引用

页码：2746 / 2752

页数：7

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