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An Efficient, Green, Microwave-assisted Synthesis of Benzo[a]furo[2, 3-c]phenazine Derivatives with TiO2-SO3H as Cost-effective and Recyclable Catalyst under Solventfree Conditions
Current Organic Synthesis ( IF 1.7 ) Pub Date : 2021-05-01 , DOI: 10.2174/1570179417666200924145534
Milad Taheri 1 , Razieh Mohebat 1 , Mohammad Hossein Moslemin 1
Affiliation  

Background: A rapid, efficient, and environmentally benign procedure for the synthesis of novel furo [2,3-c]phenazine derivatives has been developed via reactions of 2-hydroxynaphthalene-1,4-dione, arylglyoxals, and indole in the presence of TiO2-SO3H-catalyst (TSAC) as a recyclable heterogeneous catalyst under solventfree conditions using microwave irradiation.

Introduction: This study describes a successful approach for the synthesis of 2-(4-bromophenyl)-1-(1H-indol-3- yl) benzo[a]furo[2,3-c] phenazine in the presence of TiO2-SO3H-catalyst using microwave irradiation.

Objectives: In this paper, we report an efficient and convenient method for the synthesis of phenazine derivatives from benzo[a]phenazin-5-ol, arylglyoxal derivatives, and indoles in the presence of TiO2-SO3H-catalyst under microwave irradiation.

Materials and Methods: All reagents and solvents were purchased from Merck and Aldrich and used without further purification. 1H NMR spectra (DMSO) were recorded on the Gemini-500 MHz spectrophotometer with TMS as an internal standard.

Results and Discussion: To investigate the reaction conditions for the synthesis of 2-(4-bromophenyl)-1-(1Hindol- 3-yl) benzo[a]furo [2, 3-c] phenazine derivatives, we performed a reaction between 2-hydroxynaphthalene- 1,4-dione (1 mmol) and aromatic 1,2-diamines (1 mmol) as a model.

Conclusion: We demonstrated a green and straightforward procedure for the efficient synthesis of novel benzo[ a]furo[2, 3-c] phenazine derivatives in high yields via a one-pot, four-component domino protocol by using TiO2-SO3H as a mild, effective, non-toxic, and inexpensive solid acid catalyst without the addition of an organic co-solvent.



中文翻译:

在无溶剂条件下高效、绿色、微波辅助合成苯并[a]呋喃[2, 3-c]吩嗪衍生物,TiO2-SO3H 作为经济高效且可回收的催化剂

背景:通过 2-羟基萘-1,4-二酮、芳基乙二醛和吲哚在TiO 2 -SO 3 H-催化剂(TSAC)在无溶剂条件下使用微波辐射作为可回收的多相催化剂。

简介:本研究描述了在 TiO 2存在下合成 2-(4-溴苯基)-1-(1H-indol-3-yl) 苯并[a]呋喃[2,3-c]吩嗪的成功方法-SO 3 H-催化剂使用微波辐射。

目的:在本文中,我们报告了一种在 TiO 2 -SO 3 H 催化剂存在下,在微波辐射下,从苯并[a]吩嗪-5-醇、芳基乙二醛衍生物和吲哚合成吩嗪衍生物的高效便捷方法.

材料和方法:所有试剂和溶剂均购自 Merck 和 Aldrich,无需进一步纯化即可使用。1H NMR 光谱 (DMSO) 在 Gemini-500 MHz 分光光度计上记录,TMS 作为内标。

结果与讨论:为了研究合成 2-(4-溴苯基)-1-(1Hindol-3-yl) 苯并[a]呋喃 [2, 3-c] 吩嗪衍生物的反应条件,我们在2-羟基萘-1,4-二酮(1 mmol)和芳香族1,2-二胺(1 mmol)作为模型。

结论:我们展示了一种使用 TiO 2 -SO 3通过一锅四组分多米诺骨牌协议以高产率高效合成新型苯并[a]呋喃 [2, 3-c] 吩嗪衍生物的绿色且直接的程序H 作为一种温和、有效、无毒、廉价的固体酸催化剂,无需添加有机助溶剂。

更新日期:2021-03-29
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