A concise and efficient CuI-catalyzed synthesis of diimino dihydroquinazoline derivatives from isocyanides and guanidines derivatives through intramolecular C–H activation

2021 ◽  
Vol 18 ◽  
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mohammad Mahboubi-Rabbani
Keyword(s):  
Mechanistic Explanation ◽  
Analysis Data ◽  
Environmentally Benign ◽  
Elemental Analysis Data ◽  
One Pot ◽  
Activation Reaction ◽  
Short Reaction Time ◽  
Mass Spectral ◽  
Mild Conditions ◽  
High Yields

: A novel series of diimino dihydroquinazoline derivatives were synthesized from isocyanides and guanidine analogs in quantitative yields by applying an efficient, inexpensive, one-pot copper-catalyzed intramolecular C-H activation reaction under mild conditions. The structures were confirmed on the basis of IR, 1HNMR, 13C NMR, mass spectral and elemental analysis data. The protocol offers advantages like short reaction time, simple workup process, high yields, and an environmentally benign methodology. Interestingly, better results (yield = 82%) were observed in terms of the yield obtained by using a mixture of CuI, Cs2CO3 and acetonitrile as the catalyst, base and solvent, respectively. The data also suggested that compound 5i is produced with the highest yield (87%) from the corresponding diisopropyl carbon diimide, 4-nitroaniline and phenyl isocyanide. Finally, a mechanistic explanation for the reaction promoted by cuprous iodide (CuI) was proposed on the basis of previous investigations and our experimental observations.

Copper-catalyzed one-pot synthesis of benzimidazole derivatives

2008 ◽  
Vol 86 (11) ◽  
pp. 1044-1051 ◽  
Author(s):  
Hashem Sharghi ◽  
Mona Hosseini-Sarvari ◽  
Fatemeh Moeini
Keyword(s):  
Heterogeneous Catalyst ◽  
Simple Procedure ◽  
Catalytic Reactions ◽  
Environmentally Benign ◽  
Benzimidazole Derivatives ◽  
Good Recovery ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions ◽  
High Yields

A simple, efficient, and environmentally benign method has been developed for the synthesis of 2-substituted benzimidazoles through a one-pot reaction of phenylenediamines with aryl aldehydes in excellent isolated yields under mild conditions using Cu(II) complex as the selective, recyclable, and heterogeneous catalyst at ambient temperature. The Cu(II) complex as a heterogeneous catalyst can be reused in further catalytic reactions, and it was found that its activity remained largely unchanged for eight successive runs. No metal-complex leaching was observed after the consecutive catalytic reactions. The salient features of this method include mild conditions, high yields, simple procedure, and good recovery and reusability of the heterogeneous catalyst.Key words: benzimidazole, o-phenylenediamine, arylaldehydes, heterogeneous catalyst, N,N-bis (2-hydroxyphenyl)pyridine-2,6-dicarboxamide.

Iodine-Mediated Multi-Component Reactions: Readily Access to Tetrazoles and Guanidines

2020 ◽  
Vol 17 ◽  
Author(s):  
Bajivali Shaik ◽  
Mohan Seelam ◽  
Ramana Tamminana ◽  
Prasad Rao Kammela
Keyword(s):  
Reaction Time ◽  
Benzoyl Chloride ◽  
Functional Group ◽  
Molecular Iodine ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
One Pot Synthesis ◽  
High Yields

Abstract: Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excel-lent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored

Synthesis, Antimalarial Evaluation and SAR Study of Some 1,3,5-Trisubstituted Pyrazoline Derivatives

2019 ◽  
Vol 16 (10) ◽  
pp. 807-817 ◽  
Author(s):  
Shilpy Aggarwal ◽  
Deepika Paliwal ◽  
Dhirender Kaushik ◽  
Girish Kumar Gupta ◽  
Ajay Kumar
Keyword(s):  
Antimalarial Activity ◽  
Analysis Data ◽  
Docking Study ◽  
Maximum Activity ◽  
Elemental Analysis Data ◽  
Mass Spectral ◽  
Structure Activity ◽  
Pharmacokinetic Properties ◽  
Sar Study

The synthesis of a novel series of 1,3,5-trisubstitiuted pyrazoline was achieved by refluxing chalcone derivative with different heteroaryl hydrazines. The newly synthesized compounds were characterized by 1H NMR, 13CNMR, mass spectral and elemental analysis data. The synthetic series of novel pyrazoline hybrids was screened for in vitro schizont maturation assay against chloroquine sensitive 3D7 strain of Plasmodium falciparum. Most of the compounds showed promising in vitro antimalarial activity against CQ sensitive strain. The preliminary structure-activity relationship study showed that quinoline substituted analog at position N-1 showed maximum activity followed by benzothiazole substitution, while phenyl substitution lowers the antimalarial activity. The observed activity was persistent by the docking study on P. falciparum cystein protease falcipain-2. The pharmacokinetic properties were also studied using ADME prediction.

Fast and Efficient Green Procedure for the Synthesis of Benzo[5,6]chromene Derivatives and Their Sulfur Analogues in Water by Organocatalyst Potassium Phthalimide-N-oxyl

Synthesis ◽  
2020 ◽  
Vol 52 (11) ◽  
pp. 1707-1718
Author(s):  
Nasser Etivand ◽  
Jabbar Khalafy ◽  
Mohammad G. Dekamin
Keyword(s):  
Aqueous Media ◽  
Thiobarbituric Acid ◽  
Environmentally Benign ◽  
The Novel ◽  
One Pot ◽  
Synthetic Strategy ◽  
Three Component Reaction ◽  
High Yields ◽  
Green Procedure ◽  
Arylglyoxal Monohydrates

A simple, clean, straightforward, and environmentally benign one-pot, three-component reaction of various arylglyoxal monohydrates, β-naphthol, and barbituric acid [pyrimidine-2,4,6(1H,3H,5H)-trione] or thiobarbituric acid in the presence of catalytic amounts potassium phthalimide-N-oxyl (PPINO), as a mild and efficient organocatalyst in aqueous media under reflux conditions is reported. This transformation produced the novel diverse-substituted 12-benzoyl-8,12-dihydro-9H-benzo[5,6]chromeno[2,3-d]pyrimidine-9,11(10H)-diones and their sulfur analogues in 82–93% yield via filtration and without utilization of any chromatography. The high yields of products, very simple operation, easy workup, availability of starting materials, green process, and high atom-economy are the main benefits of this synthetic strategy.

CeCl3·7H2O as mild and efficient catalyst for the one-pot multicomponent synthesis of 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones

2011 ◽  
Vol 76 (4) ◽  
pp. 235-241 ◽  
Author(s):  
Li-Qiang Wu ◽  
Wei-Lin Li ◽  
Fu-Lin Yan
Keyword(s):  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Work Up

A series of new 8-aryl-7,8-dihydro[1,3]dioxolo[4,5-g]chromen-6-ones were synthesized via a three-component reaction of 3,4-methylenedioxyphenol, aromatic aldehydes and Meldrum’s acid in the presence of CeCl3·7H2O under solvent-free conditions. The method provided several advantages such as easy work-up, high yields and environmentally benign procedure.

Efficient one-pot syntheses of dibenzo[a,i]xanthene-diones and evaluation of their antioxidant activity

2012 ◽  
Vol 90 (9) ◽  
pp. 739-746 ◽  
Author(s):  
Jitender M. Khurana ◽  
Ankita Chaudhary ◽  
Anshika Lumb ◽  
Bhaskara Nand
Keyword(s):  
Antioxidant Activity ◽  
Radical Scavenging ◽  
Dpph Radical ◽  
One Pot ◽  
Short Reaction Time ◽  
One Pot Condensation ◽  
High Yields ◽  
Dpph Radical Scavenging ◽  
Task Specific Ionic Liquid ◽  
Operational Simplicity

Facile and convenient procedures for the synthesis of dibenzo[a,i]xanthene-diones have been described. The process employs one-pot condensation of aldehydes, 2-hydroxynaphthalene-1,4-dione, and 2-naphthol/2,7-dihydroxynaphthalene/2,6-dihydroxynaphthalene using catalytic sulfuric acid in water under reflux. Task-specific ionic liquid, 1-butyl-3-methylimidazolium hydrogen sulfate ([bmim]HSO4), has also been found to be an effective catalyst for this transformation. The protocols defined herein prove to be efficient in terms of high yields, operational simplicity, easy workup, and short reaction time. Also, these compounds were screened for antioxidant activity by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay.

scholarly journals A Green, Expeditious, One-Pot Synthesis of 3, 4-Dihydropyrimidin-2(1H)-ones Using a Mixture of Phosphorus Pentoxide-Methanesulfonic Acid at Ambient Temperature

2012 ◽  
Vol 2012 ◽  
pp. 1-6 ◽  
Author(s):  
Amulrao Borse ◽  
Mahesh Patil ◽  
Nilesh Patil ◽  
Rohan Shinde
Keyword(s):  
Reaction Time ◽  
Ambient Temperature ◽  
Room Temperature ◽  
Simple Procedure ◽  
Methanesulfonic Acid ◽  
Phosphorus Pentoxide ◽  
One Pot ◽  
Short Reaction Time ◽  
Solvent Free Conditions ◽  
High Yields

An expeditious, one-pot method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones using a mixture of phosphorus pentoxide-methanesulfonic acid (Eaton’s reagent) at room temperature under solvent-free conditions is described. The salient features of this method include short reaction time, green aspects, high yields, and simple procedure.

One Pot Three Component Synthesis of 9-arylpolyhydroacridine Derivatives in an Ionic Liquid Medium

2005 ◽  
Vol 2005 (9) ◽  
pp. 600-602 ◽  
Author(s):  
Yu-Ling Li ◽  
Mei-Mei Zhang ◽  
Xiang-Shan Wang ◽  
Da-Qing Shi ◽  
Shu-Jiang Tu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields ◽  
Work Up ◽  
Ionic Liquid Medium

In this paper the preparation of 3,3,6,6-tetramethyl-9-aryl-1,2,3,4,5,6,7,8,9,10- decahydroacridin-1,8-dione derivatives from aromatic aldehydes, 5,5-dimethyl-1,3- cyclohexanedione and ammonium acetate in ionic liquids [bmim+][BF4-] is described. This new method has the advantages of easier work-up, milder reaction conditions, high yields and an environmentally benign procedure compared with other methods.

Convenient and efficient synthesis of disubstituted piperazine derivatives by catalyst-free, atom-economical and tricomponent domino reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (14) ◽  
pp. 10768-10772 ◽  
Author(s):  
Hong-Ru Dong ◽  
Zi-Bao Chen ◽  
Rong-Shan Li ◽  
Heng-Shan Dong ◽  
Zhi-Xiang Xie
Keyword(s):  
Free Atom ◽  
Domino Reactions ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Piperazine Derivatives ◽  
High Yields

One-pot, atom-economical, catalyst-free and tri-component domino reactions are applied to diversity-oriented synthesis (DOS) of disubstituted piperazine derivatives under mild conditions with moderate to high yields.

scholarly journals Synthesis of biscoumarin derivatives by the reaction of aldehydes and 4-hydroxycoumarin using ruthenium (III) chloride hydrate as a versatile homogeneous catalyst

2012 ◽  
Vol 77 (4) ◽  
pp. 407-413 ◽  
Author(s):  
Khalil Tabatabaeian ◽  
Hannaneh Heidari ◽  
Alireza Khorshidi ◽  
Manouchehr Mamaghani ◽  
Nosrat Mahmoodi
Keyword(s):  
Michael Reaction ◽  
Aqueous Media ◽  
Environmentally Benign ◽  
Homogeneous Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
The One ◽  
High Yields ◽  
Chloride Hydrate ◽  
Short Times

The one-pot domino Knoevenagel-type condensation/Michael reaction of aromatic, heteroaromatic and aliphatic aldehydes with 4-hydroxycoumarin in aqueous media in the presence of ruthenium salt as homogeneous catalyst was investigated. It was found that 5 mol% of RuCl3.nH2O catalyzes biscoumarin synthesis in high yields (70-95%) under optimised, mild, green and environmentally benign reaction conditions in short times (25-35min).

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