scholarly journals l-Proline-Catalysed One-Pot Regio- and Diastereoselective Synthesis of Spiro[pyrido[2,3-d]pyrimidin-2-amine-6,5′-pyrimidines] in Water

SynOpen ◽  
2017 ◽  
Vol 01 (01) ◽  
pp. 0045-0049 ◽  
Author(s):  
Subarna Kalita ◽  
Bidyut Das ◽  
Dibakar Deka
Keyword(s):  
Reaction Time ◽  
Domino Reaction ◽  
Purification Process ◽  
Diastereoselective Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Chromatographic Techniques ◽  
High Yields ◽  
Operational Simplicity

A simple l-proline-catalysed regio- and diastereoselective synthesis of spiro[pyrido[2,3-d]pyrimidin-2-amine-6,5′-pyrimidines] in water through a strategy of one-pot multicomponent domino reaction of 2,6-diaminopyrimidin-4-one, aldehydes and barbituric acids is described. The notable advantages of the protocol are operational simplicity, mild reaction conditions, simple purification process involving no chromatographic techniques, wide substrate scope, and high yields. The method delivers the desired product within short reaction time and with a diastereoselectivity of 61:39 to 100:0, which makes the protocol highly attractive.

scholarly journals Fe3O4@chitosan-tannic acid bionanocomposite as a novel nanocatalyst for the synthesis of pyranopyrazoles

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Maryam Kamalzare ◽  
Mohammad Reza Ahghari ◽  
Mohammad Bayat ◽  
Ali Maleki
Keyword(s):  
Reaction Time ◽  
Tannic Acid ◽  
High Performance ◽  
Catalytic Performance ◽  
Natural Material ◽  
Magnetic Nanocatalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
High Yields

AbstractRecently magnetic nanocatalyst has attracted considerable attention because of its unique properties, including high performance, easy separation from the reaction mixture, and recyclability. In this study, a novel magnetic bionanocomposite was synthesized with chitosan and tannic acid as a natural material. The synthesized bionanocatalyst was characterized by essential analysis. Fe3O4@chitosan-tannic acid as a heterogeneous nanocatalyst was successfully applied to synthesize pyranopyrazole and its derivatives by a one-pot four-component reaction of malononitrile, ethyl acetoacetate, hydrazine hydrate, and various aromatic aldehyde. At the end of the reaction, the nanocatalyst was separated from the reaction mixture and was reused several times with no significant decrease in its catalytic performance. Simple purification of products, the ability for recovering and reusing the nanocatalyst, eco-friendliness, high yields of pure products, mild reaction conditions, short reaction time, non-toxicity, economically affordable are some of the advantages of using the fabricated nanocatalyst in the synthesis of pyranopyrazole.

Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds

2020 ◽  
Vol 17 (7) ◽  
pp. 518-524
Author(s):  
Shailesh Singh ◽  
Jyoti Tiwari ◽  
Deepali Jaiswal ◽  
Amit Kumar Sharma ◽  
Jaya Singh ◽  
...  
Keyword(s):  
Reaction Time ◽  
Ambient Temperature ◽  
Aromatic Aldehydes ◽  
Product Formation ◽  
One Pot ◽  
Short Reaction Time ◽  
Salient Features ◽  
High Yields ◽  
Operational Simplicity ◽  
Nucleophilic Acylation

Background: A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Materials and Methods: A flame-dried round bottom flask was charged with Imidazolium salts (3a) (0.20 mmol). Aldehyde 1a (1.0 mmol), 2-bromoacetonitrile 2 (1.0 mmol), and THF / t-BuOH 5 mL; 10:1) were added at positive nitrogen pressure followed by the addition of DBU (0.15 mmol) through stirring. The resulting yellow- orange solution was stirred at room temperature for 5-6 h. After completion of the reaction (TLC monitored), the reaction mixture was concentrated under reduced pressure. The product was purified using hexane / EtOAc (10:1) as an eluent to provide analytically pure compound 4a. Physical data of representative compounds and the NMR spectroscopic data are in agreement with the literature value. Results and Discussion: The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Conclusion: To sum up, we have developed a convenient, efficient and one-pot route for 3-oxo-3- phenylpropanenitrile synthesis from NHC promoted direct nucleophilic acylation of aromatic aldehydes using 2- bromoacetonitrile. This method provided a wide range of products and good yields. To best of our knowledge, this is the new report for the synthesis of 3-oxo-3-phenylpropanenitrile through NHC promoted nucleophilic acylation of aromatic aldehyde.

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

A One-pot Multi-component Synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates Catalysed by Oxalic Acid Dihydrate

2013 ◽  
Vol 37 (1) ◽  
pp. 40-42 ◽  
Author(s):  
Seyed Sajad Sajadikhah ◽  
Nourallah Hazeri ◽  
Malek Taher Maghsoodlou ◽  
Mostafa Sayyed Habibi-Khorassani ◽  
Khatereh Khandan-Barani
Keyword(s):  
Reaction Time ◽  
Oxalic Acid ◽  
Column Chromatography ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Oxalic Acid Dihydrate ◽  
Dialkyl Acetylenedicarboxylates ◽  
High Yields ◽  
Work Up

A simple synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot multi-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of oxalic acid dihydrate (20 mol%) as catalyst in methanol is described. This homogeneous catalytic procedure offers advantages including mild reaction conditions, good to high yields, short reaction time, simple and readily available starting materials, easy work-up and there is no need for column chromatography.

scholarly journals Microwave Assisted One Pot Synthesis of 3,4-Dihydropyrano[c]chromene Derivatives using [Emim]OH Ionic Liquid as Novel Catalyst

2019 ◽  
Vol 31 (4) ◽  
pp. 829-833
Author(s):  
D.S. Bhagat ◽  
S.G. Pande ◽  
M.V. Katariya ◽  
R.P. Pawar ◽  
P.S. Kendrekar
Keyword(s):  
Ionic Liquid ◽  
Reaction Time ◽  
High Yield ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
Aryl Aldehydes ◽  
Microwave Assisted ◽  
Novel Catalyst ◽  
Work Up

One-pot efficient protocol to the synthesis of 2-amino-5-oxo-4,5-dihydropyrano(3,2-c)chromene-3-carbonitrile derivatives via condensation of various aryl aldehydes, dicyanomethane and 4-hydroxycoumarin in presence of Emim hydroxide as an excellent homogeneous liquid catalyst. The key advantages of this methodology are mild reaction conditions, novel catalyst, short reaction time, eco-friendly, easy work-up procedure and high yield of isolation of derivatives.

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.

Multi-component synthesis of highly substituted imidazoles catalyzed by nanorod vanadatesulfuric acid

2015 ◽  
Vol 69 (11) ◽  
Author(s):  
Masoud Nasr-Esfahani ◽  
Morteza Montazerozohori ◽  
Tooba Abdizadeh
Keyword(s):  
Reaction Time ◽  
High Purity ◽  
Ammonium Acetate ◽  
Chlorosulfonic Acid ◽  
Solvent Free ◽  
One Pot ◽  
Short Reaction Time ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Tetrasubstituted Imidazoles

AbstractNanorod vanadatesulfuric acid (VSA NRs), as a recyclable and eco-benign catalyst, was used for one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles using aldehydes, benzil, benzoin or 9,10-phenanthrenequinone and ammonium acetate or aniline under solvent-free conditions providing high to excellent yields. VSA is easily prepared by a simple reaction of chlorosulfonic acid and sodium metavanadate in high purity. As compared with the conventional procedures, the present protocol offers several advantages such as simplicity of procedure, short reaction time, high yields, easy workup, recoverability and reusability of the catalyst and simple purification of the products.

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

scholarly journals Facile Synthesis of Spiro[cyclohexane-1,3’-indoline]-2,2’-diones

2019 ◽  
Vol 25 (1) ◽  
pp. 157-161 ◽  
Author(s):  
Shin-taro Katayama ◽  
Hiroshi Nishino
Keyword(s):  
Natural Products ◽  
Reaction Time ◽  
Total Synthesis ◽  
Facile Synthesis ◽  
One Pot ◽  
Short Reaction Time ◽  
High Yields

AbstractSpiro[cyclohexane-1,3’-indoline]-2,2’-diones were easily prepared in good to high yields by the oxidation of N-aryl-N-methyl-2-oxocyclohexane-1-carboxamides in one pot with a short reaction time. The spiroindolinediones could be important for the total synthesis of natural products.

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