Microwave-Assisted Cascade Cycloaddition for C–N Bond Formation: An Approach to the Construction of 1,4,5,6-Tetrahydropyrimidine and 2-Imidazoline Derivatives

Shujuan An; Bing Yin; Ping Liu; Xiangnan Li; Chen Li; Jianli Li; Zhen Shi

doi:10.1055/s-0033-1339406

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(18): 2525-2532
DOI: 10.1055/s-0033-1339406

paper

Microwave-Assisted Cascade Cycloaddition for C–N Bond Formation: An Approach to the Construction of 1,4,5,6-Tetrahydropyrimidine and 2-Imidazoline Derivatives

Shujuan An

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

,

Bing Yin

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

,

Ping Liu

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

,

Xiangnan Li

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

,

Chen Li

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

,

Jianli Li*

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

,

Zhen Shi

Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education and College of Chemistry & Materials Science, Northwest University, Xi’an Shaanxi 710069, P. R. of China Fax: +86(29)88308396 eMail: lijianli@nwu.edu.cn

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Abstract

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Abstract

An efficient strategy for the synthesis of various 1,4,5,6-tetrahydropyrimidine and 2-imidazoline derivatives has been reported. The reactions proceeded from nitriles with ethylenediamine or 1,3-diaminopropane via cascade cycloaddition in the presence of CuL₂ (L = 2-hydroxy-2-phenylacetate) to afford the corresponding 1,4,5,6-tetrahydropyrimidine or 2-imidazoline derivatives under reflux conditions or microwave irradiation in excellent yields.

Key words

catalysis - cycloaddition - nitrogen heterocycles - nitriles - synthesis

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