One-pot pseudo three-component condensation reaction of arylglyoxal monohydrates with 1-ethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione for the synthesis of new pyrano[2,3-d:6,5-d’]dipyrimidines as HIV integrase inhibitor-like frameworks using two different environmentally benign catalytic systems

2019 ◽  
Vol 16 (8) ◽  
pp. 1687-1701 ◽  
Author(s):  
Mehdi Rimaz ◽  
Hossein Mousavi ◽  
Behzad Khalili ◽  
Leila Sarvari
Keyword(s):  
Condensation Reaction ◽  
Integrase Inhibitor ◽  
Environmentally Benign ◽  
Hiv Integrase ◽  
One Pot ◽  
Catalytic Systems ◽  
Arylglyoxal Monohydrates

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.

Ionic Liquid 4-(3-Methyl-1-imidazolio)-1-butanesulfonic Acid Hydrogen Sulfate-catalyzed Synthesis of Phthalazinetrione Derivatives

2012 ◽  
Vol 67 (7) ◽  
pp. 717-724
Author(s):  
Shihua Song ◽  
Xiang Deng ◽  
Zhi Guan ◽  
Yanhong He
Keyword(s):  
Ionic Liquid ◽  
Polyethylene Glycol ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Solvent System ◽  
Environmentally Benign ◽  
Hydrogen Sulfate ◽  
One Pot ◽  
Simple Method ◽  
Peg 600

A simple method for the synthesis of phthalazinetrione derivatives by a one-pot three-component condensation reaction of phthalhydrazide, 1,3-dicarbonyl compounds and aldehydes catalyzed by the ionic liquid 4-(3-methyl-1-imidazolio)-1-butanesulfonic acid hydrogen sulfate ([BSO3HmIm]HSO4) is reported. Good to excellent yields were obtained in short reaction times in the solvent PEG 600 (polyethylene glycol 600) at 120 °C. The strategy proved to be efficient and environmentally benign. The catalyst/solvent system could easily be recovered and reused for at least 5 times without noticeable loss of activity

Environmentally benign synthesis of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates using CeO2 nanoparticles as a reusable and robust catalyst

2016 ◽  
Vol 71 (11) ◽  
pp. 1135-1140 ◽  
Author(s):  
Javad Safaei-Ghomi ◽  
Mehrnoosh Asgari-Kheirabadi ◽  
Hossein Shahbazi-Alavi
Keyword(s):  
Condensation Reaction ◽  
Ceo2 Nanoparticles ◽  
Environmentally Benign ◽  
High Yield ◽  
Synthesis And Characterization ◽  
Dimethyl Acetylenedicarboxylate ◽  
One Pot ◽  
Efficient Catalyst ◽  
Benign Synthesis

AbstractIn this work, we report the synthesis and characterization of CeO2 nanoparticles as an efficient catalyst for the preparation of methyl 6-amino-5-cyano-4-aryl-2,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates via one-pot four-component condensation reaction of dimethyl acetylenedicarboxylate, hydrazine hydrate, malononitrile, and aldehydes in aqueous medium. The use of a non-hazardous organic solvent, easy recovery of the catalyst, compatibility with various functional groups, and high yield of the products make the protocol attractive, greener, and economic.

scholarly journals Six-Step Gram Scale Synthesis of the HIV Integrase Inhibitor Dolutegravir Sodium

2021 ◽  
Author(s):  
Jule-Phillip Dietz ◽  
Tobias Lucas ◽  
Jonathan Groß ◽  
Sebastian Seitel ◽  
Jan Brauer ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Integrase Inhibitor ◽  
Active Pharmaceutical Ingredient ◽  
Ring System ◽  
Hiv Integrase ◽  
Salt Formation ◽  
One Pot ◽  
Amide Formation ◽  
Practical Synthesis

A short and practical synthesis for preparing the active pharmaceutical ingredient dolutegravir sodium was investigated. The convergent strategy developed herein starts from 3-(R)-amino-1- butanol and builds up the BC ring system in 76% isolated yield over four steps. Ring A was constructed by a one-pot 1,4-addition to diethyl-(2E/Z)-2-(ethoxymethylidene)-3-oxobutandioate and subsequent MgBr2·OEt2-mediated regioselective cyclization. Amide formation with 2,4- difluorobenzylamine was either performed from the carboxylic acid or through aminolysis of the corresponding ester precursor. Final salt formation afforded dolutegravir sodium in 48–51% isolated yield (HPLC-purity: 99.7–99.9%) over six linear steps.<br>

Three-component condensation reaction of various aldehydes, dimedone and malononitrile catalyzed by boric acid in water in comparison with multifunctional ionic liquids as green catalytic systems

2018 ◽  
Vol 73 (10) ◽  
pp. 707-712
Author(s):  
Ardeshir Khazaei ◽  
Heidar Ali Alavi Nik ◽  
Ahmad Reza Moosavi-Zare ◽  
Hadis Afshar-Hezarkhani
Keyword(s):  
Ionic Liquids ◽  
Boric Acid ◽  
Ammonium Acetate ◽  
Condensation Reaction ◽  
One Pot ◽  
Water Separation ◽  
Catalytic Systems ◽  
Hydronium Ion ◽  
Solvent Free Conditions ◽  
The One

AbstractTriethanol ammonium acetate ([TEAH]+[OAc]−) and triethanol ammonium formate ([TEAH]+[HCOO]−) as multifunctional ionic liquids and catalysts were successfully applied for the preparation of tetrahydrobenzo[b]pyrans by the one-pot three-component condensation reaction of various aldehydes, dimedone and malononitrile under solvent-free conditions. These reactions were also tested using boric acid in water. In this catalytic system, by the reaction of water with boric acid, the hydronium ion caused by water separation can catalyze the reaction.

scholarly journals One-Pot Condensation Approach for the Synthesis of Some 1,8-Dioxo-octahydroxanthenes and 14-Aryl-14H-dibenzo[a,j]Xanthenes Using Lactic Acid as an Efficient and Eco-Friendly Catalyst

2017 ◽  
Vol 25 (1) ◽  
pp. 24-37 ◽  
Author(s):  
Fatemeh Noori Sadeh ◽  
Maryam Fatahpour ◽  
Nourallah Hazeri ◽  
Malek Taher Maghsoodlou ◽  
Mojtaba Lashkari
Keyword(s):  
Lactic Acid ◽  
Reaction Time ◽  
Condensation Reaction ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
Environmental Friendliness ◽  
Solvent Free Conditions ◽  
One Pot Condensation ◽  
Convenient Approach

AbstractThe synthesis of some biologically important xanthenes, by efficient and convenient approach for one-pot condensation reaction of aldehydes and dimedone or β-naphthol in the presence of lactic acid as an efficient, inexpensive and environmental friendliness catalyst under solvent-free conditions, is presented. The merits of this reaction are higher product yields in shorter reaction time and environmentally benign reaction conditions.

scholarly journals Six-Step Gram Scale Synthesis of the HIV Integrase Inhibitor Dolutegravir Sodium

2021 ◽  
Author(s):  
Jule-Phillip Dietz ◽  
Tobias Lucas ◽  
Jonathan Groß ◽  
Sebastian Seitel ◽  
Jan Brauer ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Integrase Inhibitor ◽  
Active Pharmaceutical Ingredient ◽  
Ring System ◽  
Hiv Integrase ◽  
Salt Formation ◽  
One Pot ◽  
Amide Formation ◽  
Practical Synthesis

A short and practical synthesis for preparing the active pharmaceutical ingredient dolutegravir sodium was investigated. The convergent strategy developed herein starts from 3-(R)-amino-1- butanol and builds up the BC ring system in 76% isolated yield over four steps. Ring A was constructed by a one-pot 1,4-addition to diethyl-(2E/Z)-2-(ethoxymethylidene)-3-oxobutandioate and subsequent MgBr2·OEt2-mediated regioselective cyclization. Amide formation with 2,4- difluorobenzylamine was either performed from the carboxylic acid or through aminolysis of the corresponding ester precursor. Final salt formation afforded dolutegravir sodium in 48–51% isolated yield (HPLC-purity: 99.7–99.9%) over six linear steps.<br>

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

Novel Second Generation HIV Integrase Inhibitor-DOLUTEGRAVIR: An Emerging Weapon Against HIV

2017 ◽  
Vol 14 (3) ◽  
pp. 354-371 ◽  
Author(s):  
Vivek Jain ◽  
Diksha Gupta ◽  
Ashutosh Pareek ◽  
Yashumati Ratan
Keyword(s):  
Second Generation ◽  
Integrase Inhibitor ◽  
Hiv Integrase
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