Synthesis of Substituted Thienopyrimidinones Based on Ethyl 2-Amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate

IF 0.8 4区 化学 Q4 CHEMISTRY, ORGANIC Russian Journal of Organic Chemistry Pub Date : 2024-05-19 DOI:10.1134/s1070428024030047
S. O. Vardanyan, A. S. Avagyan, A. B. Sargsyan, S. A. Harutyunyan, H. V. Gasparyan, A. A. Aghekyan
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引用次数: 0

Abstract

Previously synthesized ethyl 2-benzamido-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylates were cyclized to 2-aryl-3-aminothieno[2,3-d]pyrimidin-4(1H)-ones by the action of hydrazine hydrate. The con­densation of ethyl 2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate with chloroacetyl chloride gave the corresponding N-substituted 2-chloroacetamide which reacted with piperidine and morpholine to produce 2-aminoacetamides, and the latter were also subjected to cyclization with hydrazine hydrate to obtain 3-amino­thienopyrimidin-4-one derivatives. The synthesized compounds were tested for antihypoxic activity.

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基于 2-氨基-4-(1,4-苯并二恶烷-2-基)噻吩-3-羧酸乙酯的取代型噻吩嘧啶酮的合成
摘要以前合成的 2-苯甲酰胺基-4-(1,4-苯并二恶烷-2-基)噻吩-3-羧酸乙酯在水合肼的作用下环化为 2-芳基-3-氨基噻吩并[2,3-d]嘧啶-4(1H)-酮。2-amino-4-(1,4-benzodioxan-2-yl)thiophene-3-carboxylate 与氯乙酰氯缩合,得到相应的 N-取代 2-氯乙酰胺,与哌啶和吗啉反应生成 2-氨基乙酰胺,后者还与水合肼发生环化反应,得到 3-氨基噻吩嘧啶-4-酮衍生物。对合成的化合物进行了抗缺氧活性测试。
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来源期刊
CiteScore
1.40
自引率
25.00%
发文量
139
审稿时长
3-6 weeks
期刊介绍: Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
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