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Bis(benzofuran-enaminone) hybrid possessing piperazine linker: Versatile precursor for microwave assisted synthesis of bis(pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines)
Synthetic Communications ( IF 2.1 ) Pub Date : 2021-01-19 , DOI: 10.1080/00397911.2020.1867745
Ahmed E. M. Mekky 1 , Mohamed S. Mohamed Ahmed 1 , Sherif M. H. Sanad 1 , Zeinab A. Abdallah 1
Affiliation  

Abstract

We reported herein efficient procedures for the synthesis of new piperazine-linked bis(pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines) using bis(benzofuran-enaminone) hybrid as a key intermediate. For this purpose, bis(enaminone) were reacted with a new series of 3-amino-4-(thiophen-2-yl)-1H-pyrazolo[3,4-b]pyridines in pyridine under microwave irradiation at 120 °C for 90 min to afford the target bis(pyrimidines). In a two-steps synthetic route, bis(enaminone) was used to prepare a novel bis(3-amino-1H-pyrazolo[3,4-b]pyridine). Next, the former hybrid was reacted with two equivalents of the appropriate enaminones as well as arylidinemalononitriles in pyridine under microwave irradiation at 120 °C for 2 h to afford the target bis(pyrimidines). Furthermore, a mixture of bis(pyrazolopyridine) reacted with two equivalents of 1,3-diketones and β-ketoesters in glacial acetic acid was microwave irradiated at 130 °C for 90 min to give bis(2,4-disubstituted pyrimidines) and bis(2-substituted pyrimidin-4(1H)-ones), respectively. The structures of the new hybrids were confirmed via considering their elemental analyses as well as their spectral data.



中文翻译:

具有哌嗪连接子的双(苯并呋喃-烯胺)杂化物:微波辅助合成双(吡啶并[2',3':3,4]吡唑并[1,5-a]嘧啶的多功能前体

抽象的

我们在这里报告了有效的程序,以双(苯并呋喃-烯胺)杂化物为主要中间体,合成了新的哌嗪连接的双(吡啶并[2',3':3,4]吡唑并[1,5- a ]嘧啶)。为此,在微波中于120°C的条件下,使双(烯胺酮)与一系列新的3-氨基-4-(噻吩-2-基)-1 H-吡唑并[3,4- b ]吡啶在吡啶中反应加热90分钟得到目标双(嘧啶)。在两步合成路线中,使用了bis(enaminone)来制备新型的bis(3-amino-1 H- pyrazolo [3,4- b]吡啶)。接下来,使前一种杂化物与二当量的合适的烯胺酮以及芳基丙二腈在吡啶中,在微波辐射下于120°C下反应2小时,以提供目标双(嘧啶)。此外,将在冰醋酸中与二当量的1,3-二酮和β-酮​​酸酯反应的双(吡唑并吡啶)的混合物在130°C微波照射90分钟,得到双(2,4-二取代的嘧啶)和双(2-取代的嘧啶-4(1 H)-1 )。新混合动力车的结构进行了确认通过考虑他们的元素分析,以及它们的光谱数据。

更新日期:2021-03-08
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