Synthesis of Ethyl 2‐Amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4H‐pyrano[3,2‐c]quinoline‐3‐carboxylates by a One‐pot, Three‐Component Reaction in the Presence of TPAB

Journal of Heterocyclic Chemistry, Journal Year: 2018, Volume and Issue: 56(1), P. 268 - 274

Published: Nov. 26, 2018

In this research, in order to synthesize a series of ethyl 2‐amino‐4‐benzoyl‐5‐oxo‐5,6‐dihydro‐4 H ‐pyrano[3,2‐ c ]quinoline‐3‐carboxylates, green and an efficient method is proposed through one‐pot three‐component reaction substituted arylglyoxals, cyanoacetate, 4‐hydroxyquinolin‐2(1 )‐one the presence terapropylammonium bromide as catalyst good yields. All synthesized new substances were characterized by FTIR, 1 H‐NMR, 13 C‐NMR spectral data elemental analysis.

Language: Английский

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An Efficient One-Pot, Four-Component Synthesis of Pyrazolo[3,4-b]pyridines Catalyzed by Tetrapropylammonium Bromide (TPAB) in Water

Australian Journal of Chemistry, Journal Year: 2018, Volume and Issue: 71(6), P. 435 - 435

Published: Jan. 1, 2018

A novel and one-pot pseudo-four-component reaction between a series of arylglyoxals, malononitrile, 3-methyl-1-phenyl-1H-pyrazol-5-amine, acetone in the presence tetrapropylammonium bromide (TPAB) has been developed to synthesize new substituted pyrazolo[3,4-b]pyridines, using water as an environmentally friendly solvent, high excellent yields.

Language: Английский

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Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide

Green Processing and Synthesis, Journal Year: 2019, Volume and Issue: 8(1), P. 533 - 541

Published: Jan. 28, 2019

Abstract Pyrazolopyridine and pyrazoloquinoline derivatives were obtained by a one-pot, three-component reaction of arylglyoxals, 3-methyl-1-aryl-1 H -pyrazol-5-amines cyclic 1,3-dicarbonyl compounds in the presence tetrapropylammonium bromide at 80°C water through Knoevenagel Micheal reactions, followed intramolecular condensation, unexpected dearoylation oxidation. Mild conditions, high yields, simplicity work up procedure, starting materials availability clean product formation are some main advantages this synthetic strategy.

Language: Английский

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One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst

Chemistry of Heterocyclic Compounds, Journal Year: 2018, Volume and Issue: 54(1), P. 51 - 57

Published: Jan. 1, 2018

Language: Английский

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One‐pot, Three‐component Synthesis of a Series of New Bis‐pyrrolo[2,3‐d]pyrimidines in the Presence of TPAB under Reflux Conditions

Journal of Heterocyclic Chemistry, Journal Year: 2018, Volume and Issue: 55(11), P. 2610 - 2618

Published: Sept. 17, 2018

A one‐pot, three‐component reaction of 1,4‐phenylene‐bis‐glyoxal, 6‐aminouracils, and dimedone or barbituric acid derivatives in the presence tetrapropylammonium bromide (5 mol%) ethanol under reflux conditions gave a series new bis‐pyrrolo[2,3‐ d ]pyrimidine high yields.

Language: Английский

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Synthesis of 4‐Hydroxy‐3‐(2‐arylimidazo[1,2‐a]pyridin‐3‐yl)quinolin‐2(1H)‐ones in the Presence of DABCO as an Efficient Organocatalyst

Journal of Heterocyclic Chemistry, Journal Year: 2019, Volume and Issue: 56(6), P. 1857 - 1865

Published: May 10, 2019

The one‐pot, three‐component, synthesis of a new series 4‐hydroxy‐3‐(2‐arylimidazo[1,2‐ ]pyridin‐3‐yl)quinolin‐2(1 H )‐ones in the presence DABCO as catalyst has been achieved using aryl glyoxal monohydrates, quinoline‐2,4(1 ,3 )‐dione, and 2‐aminopyridine 2 O/EtOH under reflux conditions. cheapness organocatalyst, simple workup, operational simplicity, regioselectivity, high yields are some advantages this protocol.

Language: Английский

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An Efficient Synthesis of Benzo[g]thiazolo[2,3‐b]quinazolin‐4‐ium and Benzo[g]benzo[4,5]thiazolo[2,3‐b]quinazolin‐14‐ium Hydroxides by a One‐pot, Three‐component Reaction under Green Conditions

Journal of Heterocyclic Chemistry, Journal Year: 2019, Volume and Issue: 56(10), P. 2912 - 2921

Published: Sept. 9, 2019

A new series of benzo[ g ]thiazolo[2,3‐ b ]quinazolin‐4‐ium and ]benzo[4,5]thiazolo[2,3‐ ]quinazolin‐14‐ium hydroxide derivatives have been synthesized by the one‐pot, three‐component reaction aryl glyoxal monohydrates, 2‐hydroxy‐1,4‐naphthoquinone, 2‐aminothiazole or 2‐aminobenzothiazole in presence triethylamine p ‐toluenesulfonic acid as organocatalysts H 2 O/acetone (2:1) at room temperature. This method offers mild conditions, excellent yields, easy workup, readily accessible starting materials catalysts.

Language: Английский

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Arylglyoxals as Versatile Synthons for Heterocycles Through Multi-Component Reactions

Current Organic Chemistry, Journal Year: 2019, Volume and Issue: 23(18), P. 1945 - 1983

Published: Oct. 24, 2019

Arylglyoxals are important synthons that have been used in the construction of a diverse spectrum compounds. The use multicomponent approaches organic synthesis due to its environmentally friendly nature is step forward towards sustainability. This review will offer reader insightful perspectives on arylglyoxals for various heterocyclic compounds like pyrroles, pyrazoles, furans, imidazoles, indoles, oxazoles, pyridines, quinazolines, pyrans, etc using approach.

Language: Английский

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Microwave‐induced one‐pot synthesis of 3‐imidazolyl indole clubbed 1,2,3‐triazole hybrids as antiproliferative agents and density functional theory study

Archiv der Pharmazie, Journal Year: 2023, Volume and Issue: 357(3)

Published: Dec. 27, 2023

Abstract Herein, we outline a highly efficient PEG‐4000‐mediated one‐pot three‐component reaction for the synthesis of 3‐imidazolyl indole clubbed 1,2,3‐triazole derivatives ( 5a–r ) at up to 96% yield as antiproliferative agents. This protocol offers advantages an environmentally benign reaction, excellent yield, quick response time, and operational simplicity triggered by copper catalyst under microwave irradiation. All synthesized compounds were tested activity against six human solid tumor cell lines, that is, A549 SW1573 (nonsmall lung), HBL100 T‐47D (breast), HeLa (cervix), WiDr (colon). Among them, compounds, 5g–j , 5m 5p demonstrated effective action with GI 50 values 10 μM. Furthermore, density functional theory (DFT) calculations performed all molecules through geometry optimizations, frontier molecular orbital approach, electrostatic potential (MESP). The theoretical DFT calculation was using DFT/B3LYP/6‐31+G (d,p) basis set. Moreover, biological reactivity representative compared theoretically calculated quantum chemical descriptors MESP 3D plots. We also investigated drug‐likeness characteristic absorption, distribution, metabolism, excretion, toxicity (ADMET) prediction. In general, our approach enables friendly access prospective

Language: Английский

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Water-acetic acid mediated an efficient and eco-friendly protocol for the one-pot synthesis of bis-isoxazolyl amino dihydro-1 H -indol-4(5 H )-ones under mild reaction conditions

Tetrahedron Letters, Journal Year: 2017, Volume and Issue: 58(51), P. 4790 - 4795

Published: Nov. 13, 2017

Language: Английский

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