Oxidant/Solvent-Controlled I2-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions

被引：20

作者：

Ma, Renchao ^{[1
,2
]}

Ding, Yuxin ^{[1
,2
]}

Chen, Rener ^{[1
,2
]}

Wang, Zhiming ^{[1
,2
]}

Wang, Lei ^{[1
,2
]}

Ma, Yongmin ^{[1
,2
]}

机构：

[1] Taizhou Univ, Inst Adv Studies, Taizhou 318000, Peoples R China

[2] Taizhou Univ, Sch Pharmaceut & Chem Engn, Taizhou 318000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

关键词：

ONE-POT SYNTHESIS; OXIDATIVE SYNTHESIS; 2-SUBSTITUTED BENZIMIDAZOLES; SUBSTITUTED BENZOTHIAZOLES; ARYL KETONES; EFFICIENT; CYCLIZATION; ACCESS; MILD; ACID;

D O I：

10.1021/acs.joc.0c02095

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I-2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO2 or in 1,4-dioxane containing PhNO2, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO2/I-2 co-catalytic system is proposed first time.

引用

页码：310 / 321

页数：12

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