Synthesis ( IF 2.2 ) Pub Date : 2019-02-25 , DOI: 10.1055/s-0037-1611211 Dmitry Dar’in 1 , Grigory Kantin 1 , Olga Bakulina 1 , Raivis Žalubovskis 2 , Mikhail Krasavin 1
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Abstract
For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E-configured coupling products while compounds mostly featured in the literature were predominantly Z-configured. The possibility for preparing a library of 4-arylpyridine-2,6(1H,3H)-diones has been exemplified.
For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E-configured coupling products while compounds mostly featured in the literature were predominantly Z-configured. The possibility for preparing a library of 4-arylpyridine-2,6(1H,3H)-diones has been exemplified.
中文翻译：
通过谷氨酸二甲酯与甲苯磺酸zon烯酮的Heck-Matsuda芳基化反应灵活地进入3-芳基-2-烯二酸
抽象的
为了制备对硫氧还蛋白还原酶的亲核硒代半胱氨酸残基具有可调反应性的迈克尔受体的化合物文库，需要一定范围的3-芳基戊二酸。当时的现有方法范围有限或涉及多个步骤。已经开发出迄今未描述的用于乙酸钯（II）在位置3上直接催化戊二酸二甲酯的芳基化的方案，其具有多种套杂的甲苯磺酸二氮唑鎓盐，随后进行水解。这种通常高产的两步序列显示了提供E-构型的偶联产物的倾向，而文献中最常见的化合物主要是Z-构型的。制备4-芳基吡啶-2,6（1 H，3H-二酮已经被举例说明。
为了制备对硫氧还蛋白还原酶的亲核硒代半胱氨酸残基具有可调反应性的迈克尔受体的化合物文库，需要一定范围的3-芳基戊二酸。当时的现有方法范围有限或涉及多个步骤。已经开发出迄今未描述的用于乙酸钯（II）在位置3上直接催化戊二酸二甲酯的芳基化的方案，其具有多种套杂的甲苯磺酸二氮唑鎓盐，随后进行水解。这种通常高产的两步序列显示了提供E-构型的偶联产物的倾向，而文献中最常见的化合物主要是Z-构型的。制备4-芳基吡啶-2,6（1 H，3H-二酮已经被举例说明。
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