Synthesis of substituted methylidenepyrimidobenzothiazolones as potential cytotoxic agents

被引：6

作者：

Modranka, Jakub ^{[1
]}

Pietrzak, Anna ^{[2
]}

Wolf, Wojciech M. ^{[2
]}

Janecki, Tomasz ^{[1
]}

机构：

[1] Lodz Univ Technol, Inst Organ Chem, Zeromskiego 116, PL-90924 Lodz, Poland

[2] Lodz Univ Technol, Inst Gen & Ecol Chem, Zeromskiego 116, PL-90924 Lodz, Poland

来源：

ARKIVOC | 2017年

关键词：

Pyrimidobenzothiazolones; methylidenepyrimidobenzothiazolones; Michael addition; Horner-Wadsworth-Emmons olefination; phosphorylated azaheterocycles; ANTITUMOR-ACTIVITY; SERIES; 3-METHYLIDENECHROMAN-2-ONES; BENZOTHIAZOLE; HETEROCYCLES; DERIVATIVES; LACTONES; ACIDS;

D O I：

10.3998/ark.5550190.p009.707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of biologically important substituted 3-methylidene-2,3-dihydro-4H-pyrimido[2,1-b][1,3]benzothiazol-4-ones and 3-methylidene-3,4-dihydro-2H-pyrimido[2,1-b][1,3]benzothiazol-2-ones was synthesized applying Horner-Wadsworth-Emmons methodology for the introduction of exo-methylidene bond onto a heterocyclic ring. Crucial in this approach, phosphonates were prepared by the reaction of ethyl 2-diethoxyphosphoryl-3-methoxyacrylate or ethyl 2-diethoxyphosphoryl-3-chloroacrylate with 2-aminobenzothiazoles, followed by addition of Grignard reagents to the obtained 3-diethoxyphosphoryl-4H-pyrimidobenzothiazol-4-ones or 3-diethoxyphosphoryl-2H-pyrimido[2,1-b][1,3]benzothiazol-2-ones, respectively. Surprising, ambident behavior of 2-aminobenzothiazoles towards ethyl 2-diethoxyphosphoryl-3-methoxyacrylate and ethyl 2-diethoxyphosphoryl-3-chloroacrylate is also discussed.

引用

页码：118 / 137

页数：20

共 28 条

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