First example of isatin used in four-component synthesis of ionic unsymmetrical scaffold with three different heterocyclic rings

IF 1.8 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Mendeleev Communications Pub Date : 2024-11-01 DOI:10.1016/j.mencom.2024.10.030
Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Artem N. Fakhrutdinov, Mikhail P. Egorov
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Abstract

The new type of four-component tandem Knoevenagel–Michael reaction was found: isatins, barbituric acids, malononitrile and morpholine at ambient temperature and without catalysts selectively form new non-symmetrical ionic scaffold, namely, morpholin-4-ium 5-(3-dicyanomethyl-2-oxoindolin-3-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydropyrimidin-4-olate derivatives, in 80-98% yields. Their structure was confirmed using 2D NMR such as 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC correlation experiments. The products seem promising as they contain three different pharmacologically active heterocyclic rings.

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isatin在含三个不同杂环的离子不对称支架的四组分合成中的第一个例子
发现了一种新型的四组分串联Knoevenagel-Michael反应:isatins、巴比妥酸、丙二腈和啉在常温下无催化剂条件下选择性地形成新的非对称离子支架,即morpholin-4-ium 5-(3-二氰甲基-2-氧吲哚啉-3-基)-1,3-二甲基-2,6-二氧基-1,2,3,6-四氢嘧啶-4-olate衍生物,收率为80-98%。通过二维核磁共振1H-1H COSY、1H-13C HSQC和1H-13C HMBC相关实验证实了它们的结构。这些产品似乎很有希望,因为它们含有三种不同的药理活性杂环。
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来源期刊
Mendeleev Communications
Mendeleev Communications 化学-化学综合
CiteScore
3.00
自引率
21.10%
发文量
226
审稿时长
4-8 weeks
期刊介绍: Mendeleev Communications is the journal of the Russian Academy of Sciences, launched jointly by the Academy of Sciences of the USSR and the Royal Society of Chemistry (United Kingdom) in 1991. Starting from 1st January 2007, Elsevier is the new publishing partner of Mendeleev Communications. Mendeleev Communications publishes short communications in chemistry. The journal primarily features papers from the Russian Federation and the other states of the former USSR. However, it also includes papers by authors from other parts of the world. Mendeleev Communications is not a translated journal, but instead is published directly in English. The International Editorial Board is composed of eminent scientists who provide advice on refereeing policy.
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