Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction

Keivanloo, Ali; Fakharian, Mahsa; Nabid, Mohammad Reza; Amin, Amir Hossein

doi:10.1007/s13738-018-1492-y

Cited by 9 publications

(2 citation statements)

References 32 publications

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“…In recent years there have been reported procedures for the synthesis of new linkage compounds from 1,2,3-triazoles and heterocyclic moieties through copper-catalyzed azide-alkyne cycloaddition reaction. [23][24][25] Recently, we have successfully used a metal-catalyzed reaction for the construction of new heterocyclic compounds, [26][27][28][29][30] in the particular synthesis of hybrid structures derived from 1,2,3-triazole and other heterocycles. [31,32] Here, in this study, we describe the preparation of novel 1,2,3-triazole-linked 1,2,4-triazino [5,6-b] At first, the starting material 4,5-dihydro-3H-1,2,4-triazino [5,6-b]indole-3-thion (2) was prepared by the reaction of isatin (1) with thiosemicarbazide in water (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Click Synthesis of 1,2,3‐Triazoles‐Linked 1,2,4‐Triazino[5,6‐b]indole, Antibacterial Activities and Molecular Docking Studies

et al. 2020

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The reaction of 4,5-dihydro- 3H-1,2,4-triazino[5,6-b]indole-3-thion with propargyl bromide, in EtOH at 80°C, produces monopropargylated 3-(prop-2-one-1-ylthio)-5H-1,2,4-triazino[5,6-b] indole. Further reaction of this compound with propargyl bromide, in DMF in the presence of K 2 CO 3 at room temperature, produced successfully double-propargylated 5-The Cu(I)-catalyzed click reaction of these propargylated compounds with different aromatic azides at room temper-ature, afforded new derivatives of 1,2,3-triazoles-linked 1,2,4triazino [5,6-b]indole with high yields. The in vitro antibacterial activities of the novel 1,2,3-triazoles were screened. The binding modes of these compounds to three enzyme active sites were determined by a molecular docking study. Docking studies demonstrated the most potent compounds; and binding maps revealed that the activities might be attributed to the hydrophobic interactions, hydrogen bonds, cation-π and π-π contacts with the active sites. Figure 7. Binding mode of compound 7 a (A), 7 b (B) and 7 c (C) in the active site. ChemistrySelectFull Papers

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Section: Resultsmentioning

confidence: 99%

Click Synthesis of 1,2,3‐Triazoles‐Linked 1,2,4‐Triazino[5,6‐b]indole, Antibacterial Activities and Molecular Docking Studies

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“…[19][20][21][22][23][24] The roles of a ligand in the rate acceleration were attributed to the stabilization of the Cu(I) spices by avoiding oxidation, and increase of Cu(I) species by generating an efficient concentration through the catalytic cycle. [29][30][31][32][33] In the present study, we presented the use of sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate as an efficient ligand for the synthesis of novel 1,2,3-triazoles-linked quinazolinone scaffold in water. [26][27][28] Recently, we reported our studies for the synthesis of new biologically active structures.…”

Section: Introductionmentioning

confidence: 99%

Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold

Keivanloo

Bakherad

Mokhtarei

2019

Journal of Heterocyclic Chem

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Water soluble sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate ligand was used successfully for the preparation of 1,2,3-triazoles pharmacophore linked-quinazolinone scaffold. The reaction of ethyl 4-oxo-3,-4-dihydroquinazoline-2-carboxylate and related amide compounds with propargyl bromide afforded ethyl 4-oxo-3-(prop-2-yn-1-yl)-3,4-dihydro quinazoline-2-carboxylate and its amide derivatives. The reaction of propargylated compounds with azides catalyzed by copper (II) salt, in the presence of Sodium 4-amino-5-hydroxy-7-sulfonaphthalene-2-sulfonate as a ligand in water produced novel 1,2,3-triazole pharmacophore linked-quinazolinone-4-one scaffold with high-to-excellent yields. The ligand assisted in the click reaction and reduced loading of copper salt to 2 mol%. Simplicity, short reaction times, use of water as green solvent, and low catalyst loading are the main advantages of this procedure.

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New Pd‐Mediated Cascade Reactions for Synthesis of Novel Functionalized 1,3‐Oxazole‐Linked Quinoxaline Amines

et al. 2019

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A number of functionalized 1,3-oxazoles-linked amine-substituted quinoxalines were synthesized via one-pot Pd-catalyzed reactions in high yields. The cascade reactions of benzoyl chlorides, proprgylamine, and 3-chloroquinoxaline-2-amines catalyzed by Pd-Cu in the presence of Et 3 N afforded new 3-(amine-substituted)quinoxalin-2-yl)(2-aryl-1,3-oxazol-5-yl)methanone derivatives at 70°C. The reactions commenced with the production of N-propargylamides from benzoyl chlorides and proprgylamine, and proceeded through the Sonogashira coupling reactions with 3-chloroquinoxaline-2-amines followed by the in situ ring closure of the resulting intermediates to give the target products. The use of primary 3-chloroquioxaline-2amines revealed that the cyclization step was regioselective and that pyrrolo[2,3-b]quinoxalines were not prepared in this process.

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Novel one-pot synthesis of 1-alkyl-2-(aryloxy)methyl-1H-pyrrolo[2,3-b]quinoxalines via copper-free Sonogashira coupling reaction

Cited by 9 publications

References 32 publications

Click Synthesis of 1,2,3‐Triazoles‐Linked 1,2,4‐Triazino[5,6‐b]indole, Antibacterial Activities and Molecular Docking Studies

Click Synthesis of 1,2,3‐Triazoles‐Linked 1,2,4‐Triazino[5,6‐b]indole, Antibacterial Activities and Molecular Docking Studies

Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold

New Pd‐Mediated Cascade Reactions for Synthesis of Novel Functionalized 1,3‐Oxazole‐Linked Quinoxaline Amines

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