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微波辅助、连续两步、一锅法合成含三/四取代咪唑衍生物的新型咪唑并[1,2-a]嘧啶

Microwave assisted, sequential two-step, one-pot synthesis of novel imidazo[1,2-a]pyrimidine containing tri/tetrasubstituted imidazole derivatives.

作者信息

GÜngÖr Tuğba

机构信息

Department of Chemistry, Faculty of Sciences and Arts, Natural Products and Drug Research Laboratory,Çanakkale Onsekiz Mart University, Çanakkale Turkey.

出版信息

Turk J Chem. 2021 Feb 17;45(1):219-230. doi: 10.3906/kim-2009-40. eCollection 2021.

DOI:10.3906/kim-2009-40
PMID:33679165
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7925308/
Abstract

A series of novel imidazo[1,2- ]pyrimidine containing tri/tetrasubstituted imidazole derivatives (1-10) has been synthesized via sequential two-step, one-pot, multicomponent reaction using imidazo[1,2- ]pyrimidine-2-carbaldehyde, benzil, primary amines, and ammonium acetate catalyzed by -toluenesulfonic acid under microwave-assisted conditions. The results showed that target compounds can be obtained from a wide range of primary amines bearing different functional groups with moderate to good yields (46%-80%) under optimum reaction conditions. This method provides a green protocol for imidazo[1,2- ]pyrimidine containing tri/tetrasubstituted imidazole derivatives due to ethyl alcohol as a green solvent, microwave irradiation as a greener heating method and one-pot multicomponent reaction as a green technique. The synthesized compounds have been elucidated using various spectroscopic tools such as FT-IR, H NMR, C NMR, and MS.

摘要

通过在微波辅助条件下,以咪唑并[1,2 - ]嘧啶 - 2 - 甲醛、联苯甲酰、伯胺和乙酸铵为原料,对甲苯磺酸催化,经连续两步一锅多组分反应,合成了一系列含三/四取代咪唑的新型咪唑并[1,2 - ]嘧啶衍生物(1 - 10)。结果表明,在最佳反应条件下,目标化合物可以从多种带有不同官能团的伯胺中获得,产率中等至良好(46% - 80%)。由于使用乙醇作为绿色溶剂、微波辐射作为更环保的加热方法以及一锅多组分反应作为绿色技术,该方法为含三/四取代咪唑的咪唑并[1,2 - ]嘧啶衍生物提供了一种绿色合成方案。已使用傅里叶变换红外光谱(FT - IR)、核磁共振氢谱(¹H NMR)、核磁共振碳谱(¹³C NMR)和质谱(MS)等各种光谱工具对合成的化合物进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/24707ae2c236/turkjchem-45-219-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/3b252913891b/turkjchem-45-219-fig001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/6621045723a2/turkjchem-45-219-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/a9c7629aaefa/turkjchem-45-219-fig002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/24707ae2c236/turkjchem-45-219-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/3b252913891b/turkjchem-45-219-fig001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/6621045723a2/turkjchem-45-219-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/a9c7629aaefa/turkjchem-45-219-fig002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/21f4/7925308/24707ae2c236/turkjchem-45-219-sch002.jpg

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