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L-(+)-色氨酸甲酯衍生的聚合物微珠作为一种高效的非均相催化剂用于绿色合成2-氨基-4-(硝基甲基)-4-色烯-3-腈。

L-(+)-Tryptophan methyl ester derived polymeric microbeads as an efficient heterogeneous catalyst for green synthesis of 2-amino-4-(nitromethyl)-4-chromene-3-carbonitriles.

作者信息

Haliç Poslu Ayşe, Osman Bilgen, Kaya Yunus, Koz Ömer, Koz Gamze

机构信息

Department of Chemistry, Faculty of Engineering and Natural Sciences, Bursa Technical University, Bursa, Turkey.

Department of Chemistry, Faculty of Arts and Science, Bursa Uludağ University, Bursa, Turkey.

出版信息

Turk J Chem. 2022 Jul 19;46(5):1642-1650. doi: 10.55730/1300-0527.3467. eCollection 2022.

DOI:10.55730/1300-0527.3467
PMID:37529754
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10390106/
Abstract

The cross-linked microbeads with average diameter of 106-300 μm, [poly(EGDMA-MATrp)], were obtained by copolymerization reaction of N-methacryloyl-L-(+)-tryptophan methyl ester (MATrp) with ethylene glycol dimethacrylate (EGDMA) and successfully applied as a heterogeneous catalyst in conjugate addition reaction of nitromethane to substituted 2-iminochromenes in aqueous media. A variety of 2-amino-4-(nitromethyl)-4-chromene-3-carbonitriles has been synthesized in good yields. Polymeric microbeads were very durable and reused 5 times without a significant loss of activity. DFT calculations and experimental results revealed the significant role of π-π interactions as well as hydrogen bonding in the reaction mechanism.

摘要

通过N-甲基丙烯酰基-L-(+)-色氨酸甲酯（MATrp）与乙二醇二甲基丙烯酸酯（EGDMA）的共聚反应，得到了平均直径为106 - 300μm的交联微珠[聚（EGDMA - MATrp）]，并成功地将其用作水介质中硝基甲烷与取代的2-亚氨基色烯共轭加成反应的多相催化剂。以良好的产率合成了多种2-氨基-4-(硝基甲基)-4-色烯-3-腈。聚合物微珠非常耐用，可重复使用5次且活性没有明显损失。密度泛函理论计算和实验结果揭示了π-π相互作用以及氢键在反应机理中的重要作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/8cf94779c5f1/turkjchem-46-5-1642f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/0deba9cf6aae/turkjchem-46-5-1642f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/eb57efa1dcd4/turkjchem-46-5-1642f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/73c71262ef6a/turkjchem-46-5-1642f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/98cf57b448c5/turkjchem-46-5-1642f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/8cf94779c5f1/turkjchem-46-5-1642f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/0deba9cf6aae/turkjchem-46-5-1642f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/eb57efa1dcd4/turkjchem-46-5-1642f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/73c71262ef6a/turkjchem-46-5-1642f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/98cf57b448c5/turkjchem-46-5-1642f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/32e4/10390106/8cf94779c5f1/turkjchem-46-5-1642f5.jpg

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