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A Vanadium-Catalyzed Synthesis of Fully Substituted Pyrroles
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2021-01-04 , DOI: 10.1021/acs.joc.0c02451
Patrycja Paciorek 1 , Janusz Szklarzewicz 1 , Bartosz Trzewik 1 , Dariusz Cież 1 , Wojciech Nitek 1 , Maciej Hodorowicz 1 , Anna Jurowska 1
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We present a straightforward, fast, inexpensive, and environmentally friendly synthesis of 1,2,3,4,5-pentasubstituted derivatives of pyrrole, which were produced in one-pot reactions of 3-oxoanilides with hydrazides of carboxylic acids, catalyzed by 10 mol % VOSO4·H2O. The reactions were carried out in ethanol in contact with air as the oxidant. The 19 pyrroles obtained were usually crystalline and did not require purification. The reaction tolerates various substituents in both substrates. All products were characterized by infrared, nuclear magnetic resonance, and ultraviolet–visible spectroscopy and elemental analysis. The molecular structures of the products and the intermediates were unambiguously determined by X-ray single-crystal analysis.

中文翻译:

钒催化的全取代吡咯的合成

我们介绍了吡咯的1,2,3,4,5-五取代衍生物的直接,快速,廉价和环保的合成方法,该合成方法是在3-氧苯胺与羧酸酰肼的一锅反应中,由10催化摩尔%VOSO 4 ·H 2 O的反应在乙醇中与空气接触作为氧化剂进行。所获得的19种吡咯通常是结晶的,不需要纯化。该反应容许两种底物中的各种取代基。所有产品均具有红外,核磁共振,紫外可见光谱和元素分析的特征。通过X射线单晶分析明确确定了产物和中间体的分子结构。
更新日期:2021-01-16
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