On the Reactivity of N-Substituted Imidates Towards 1,4-Bisnucleophiles: An Experimental and Theoretical Study

被引：0

作者：

Ouni, Sarra ^{[1
,2
]}

Abdelli, Abderrahmen ^{[1
]}

Gaucher, Anne ^{[2
]}

Arfaoui, Youssef ^{[3
]}

Prim, Damien ^{[2
]}

Efrit, Mohamed Lotfi ^{[1
]}

机构：

[1] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl Select Evaluat Dacti, Campus Univ, Tunis 2092, Tunisia

[2] Univ Paris Saclay, Inst Lavoisier Versailles, CNRS, UVSQ, F-78035 Versailles, France

[3] Univ Tunis El Manar, Fac Sci, Dept Chim, Lab Caracterisat Applicat & Modelisat Mat LR18ES0, Tunis 2092, Tunisia

来源：

CHEMISTRY AFRICA-A JOURNAL OF THE TUNISIAN CHEMICAL SOCIETY | 2022年 / 5卷 / 05期

关键词：

Imidates; 1,4-Binucleophiles; Heterocycles; DFT; CATALYZED SYNTHESIS; CASCADE SYNTHESIS; BENZIMIDAZOLES; QUINAZOLINES; ALKOXYAMIDE; HALIDES; COPPER;

D O I：

10.1007/s42250-022-00452-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper sets out to describe the reaction of N-acyl and N-ethoxycarbonyl imidates with 1,4-bisnucleophiles. The reaction selectively led to 5-membered heterocycles in good yields instead of expected 7-membered ring systems. Using mild reaction conditions, we synthesized 2-imidazoline, benzimidazolines, 2-oxazoline, 2-thiazoline and 2-dithiolane derivatives. Experimental results are supported by theoretical DFT calculations. Our approach has been further extended to 1,5 bis amines towards tetrahydropyrimidine scaffolds. [GRAPHICS] .

引用

页码：1265 / 1273

页数：9

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