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Tetramethylguanidine-functionalized nanosize γ-Al 2 O 3 as a novel and efficient catalyst for the four-component synthesis of pyrazolopyranopyrimidine derivatives
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2021-01-02 , DOI: 10.1007/s13738-020-02123-6
Mahnoush Keshavarz , Manouchehr Mamaghani , Mohammad G. Dekamin , Mohammad Nikpassand

Abstract

A heterogeneous organic–inorganic hybrid durable nanocatalyst γ-Al2O3@Silane-TMG was prepared by covalently functionalization of nano-γ-Al2O3 through anchored 3-chloropropyl- trimethoxysilane with 1,1,3,3-tetramethylguanidine (TMG). The structure of the catalyst was characterized by various techniques including FT-IR, XRD, SEM, EDX and TGA analyses. The synthesized nanocatalyst was successfully used in an efficient and green four-component synthesis of pyrazolopyranopyrimidine derivatives using ethyl acetoacetate, hydrazine hydrate, arylaldehydes and barbituric acid (or thiobarbituric acid) in H2O at 40 ºC. This practical method produced the desired products at reduced reaction times (10–25 min) and high to excellent yields (85–98%). The main advantages of this practical method are the use of heterogeneous basic nanocatalyst, simple work-up procedure with no need to chromatographic purification, affording highly selective conversion and recyclability of the catalyst which could be used in 5 cycles with only a small decrease in its activity.

Graphic abstract



中文翻译:

四甲基胍官能化的纳米γ-Al2 O 3作为吡唑并吡喃并嘧啶衍生物四组分合成的新型高效催化剂

摘要

异构有机-无机混合耐用纳米催化剂的γ-Al 2 ö 3 @硅烷TMG物通过共价官能化制备纳米的γ-Al 2 ö 3通过锚定的3-氯丙基三甲氧基硅烷与1,1,3,3-四甲基胍( TMG)。催化剂的结构通过多种技术进行表征,包括FT-IR,XRD,SEM,EDX和TGA分析。所合成的纳米催化剂已成功用于H 2中使用乙酰乙酸乙酯,水合肼,芳醛和巴比妥酸(或硫代巴比妥酸)的高效,绿色四组分合成吡唑并吡喃并嘧啶衍生物。O在40ºC下。这种实用的方法以减少的反应时间(10–25分钟)和高至优异的产率(85–98%)生产了所需的产品。该实用方法的主要优点是使用非均相碱性纳米催化剂,无需色谱纯化即可进行简单的后处理程序,提供了高度选择性的转化和可循环利用的催化剂,该催化剂可在5个循环中使用,但其使用量仅略有减少活动。

图形摘要

更新日期:2021-01-02
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