Palladium-catalyzed amination of 2-chlorothienopyridone with primary aromatic amines

Cogent Chemistry Pub Date : 2019-01-01 DOI:10.1080/23312009.2019.1567894

Samir A. Al-taweel, Salah A Al-Trawneh, Wal'A M. Al-Trawneh

引用次数: 1

Abstract

Abstract A series of ethyl 7-cyclopropyl-2-(arylamino)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (9a-d) were prepared by coupling of ethyl 7-cyclopropyl-2-chloro-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylate (8) with primary aromatic amines via palladium-catalyzed amination using palladium acetate Pd(OAc)2 in the presence of cesium fluoride in good yields. The new compounds were characterized by 1H-NMR, 13C-NMR, mass spectrometry, high resolution mass spectrometry and elemental analysis. 7-cyclopropyl-2-(phenylamino)-3-nitro-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid (10a) showed weak activity against E.aerogenas and S.aureus bacteria.

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钯催化2-氯噻吩并吡啶酮与伯芳香胺的胺化反应

摘要在氟化铯存在下，采用钯催化醋酸钯Pd(OAc)2，将7-环丙基-2-(芳基氨基)-3-硝基-4-氧-4,7-二氢噻吩[2,3-b]吡啶-5-羧酸酯(8)与伯胺偶联，制备了一系列7-环丙基-2-(芳基氨基)-3-硝基-4-氧-4,7-二氢噻吩[2,3-b]吡啶-5-羧酸酯(9a-d)。通过1H-NMR、13C-NMR、质谱、高分辨率质谱和元素分析对化合物进行了表征。7-环丙基-2-(苯胺)-3-硝基-4-氧-4,7-二氢噻吩[2,3-b]吡啶-5-羧酸(10a)对e .气原菌和金黄色葡萄球菌的活性较弱。

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来源期刊

Cogent Chemistry CHEMISTRY, MULTIDISCIPLINARY-

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