Microwave-assisted synthesis of indole-2-carboxylic acid esters in ionic liquid

Gu, Lijun; Li, Xiangguang

doi:10.1590/s0103-50532011001100003

Cited by 11 publications

(3 citation statements)

References 13 publications

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“…Twenty-five aromatic and heteroaromatic haloaldehydes and haloketones were cyclocondensated with ethyl isocyanoacetate to give 2-ethoxycarbonylindoles in a reaction catalyzed by CuI and [bmim]OH, under MW irradiation [130] (Scheme 49). Scheme 49.…”

Section: Cyclization Reactions To Heterocycles With C-c Bond Formationmentioning

confidence: 99%

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

et al. 2017

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Abstract:The quest for sustainable processes is becoming more and more important, with catalysis playing a major role in improving atom economy and reducing waste. Organic syntheses with less need of protecting/de-protecting steps are highly desirable. The combination of microwave irradiation, as energy source, with ionic liquids, as both solvents and catalysts, offered interesting solutions in recent years. The literature data of the last 15 years concerning selected reactions are presented, highlighting the importance of microwave (MW) technology coupled with ionic liquids.

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Section: Cyclization Reactions To Heterocycles With C-c Bond Formationmentioning

confidence: 99%

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

et al. 2017

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“…The title compound was prepared following the reported procedure [1]. In a typical experiment 0.2 g (yield 89%) of the title compound was obtained.…”

Section: Source Of Materialsmentioning

confidence: 99%

Crystal structure of ethyl 5-chloro-2-indolecarboxylate, C11H10ClNO2

Wu¹,

Liu²,

Wu³

et al. 2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was prepared following the reported procedure [1]. In a typical experiment 0.2 g (yield 89%) of the title compound was obtained. The single crystals were obtained by slow evaporation from an ethanol solution at room temperature. Experimental detailsHydrogen atoms bonded to carbon were positioned geometrically, with C-H = 0.95 to 0.99 Å, and constrained to ride on their parent atoms, with U iso (H) =1.2U eq (C). Positional parameters and the U iso value of the hydrogen atom H1N were refined freely. DiscussionThe indole moiety is a heterocycle found in a large array of natural products and pharmaceuticals possessing anti-allergic [2], central-nervous-system depressant [3], muscle relaxant [4], and anti-cancer [5,6] properties. Consequently, synthetic approaches toward indoles have long been a topic of fundamental interest to organic and medicinal chemists [7,8]. The Fischer indole synthesis is the most widely used method for the preparation of indole derivatives [9,10]. The crystal structure of methyl indole-3-carboxylate [11], as well as the structures of some esters of indole-2-carboxylic acid are known [12][13][14]. The title crystal structure is built by the C 11 H 10 ClNO 2 molecules, in which all bond lengths and angles are in normal ranges. The finding of a nearly planar molecule is in good agreement with the structure of methyl 5-chloro-1H-indole-2-carboxylate [15]. An examination of the deviations from the least-squares planes through individual rings shows that rings A (N1/C1/C2/C3/C8) and B (C3-C8) are each planar. The indole ring system is planar, with a puckering amplitude Q = 0.0069 Å [16]. The mean plane of the methoxy carbonyl group is s slightly twisted with a dihedral angle of 2.06(15)°with respect to the indole ring system. Intermolecular N-H···O hydrogen bonds between C=O and N1-H1N link the molecules, forming centrosymmetric dimers.

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“…Among numerous synthetic methodologies of α-aminophosphonate, the most noteworthy and remarkable one is Kabachnik-Fields reaction, generally using amines, dialkyl phosphites and carbonyl compounds as the reactants. [8] In connection with our ongoing project on the Cu-catalyzed reaction, [9] we herein describe a new strategy to construct α-aminophosphonates containing benzothiazole moiety.…”

Section: Introductionmentioning

confidence: 99%

Novel Synthetic Route to α‐Aminophosphonates Containing Benzothiazole Moiety

Wang

Huang

et al. 2012

Chin. J. Chem.

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A novel and efficient synthetic route to α-aminophosphonates containing benzothiazole moiety via a cascade three-component reaction from conveniently available starting materials has been developed. The target compounds 3a-3g, 7 and 8a, 8b were evaluated for their anticancer activities against the cancer cell line HL-60 in vitro by the MTT method. Compound 3g showed good cancer inhibitory activity against the tested cell line. Further study is necessary to find out the potential antitumor activities.

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Microwave-assisted synthesis of indole-2-carboxylic acid esters in ionic liquid

Cited by 11 publications

References 13 publications

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

Crystal structure of ethyl 5-chloro-2-indolecarboxylate, C11H10ClNO2

Novel Synthetic Route to α‐Aminophosphonates Containing Benzothiazole Moiety

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