One-pot and Three-Component Synthesis of α-Benzylamino Pyrones

2017 ◽  
Vol 41 (1) ◽  
pp. 42-44 ◽  
Author(s):  
Jilla Sanchooli ◽  
Alireza Hassanabadi
Keyword(s):  
Oxalic Acid ◽  
Aqueous Media ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Secondary Amines ◽  
Reaction Conditions ◽  
One Pot ◽  
Aerobic Conditions ◽  
Salient Features ◽  
High Yields

The synthesis of α-benzylamino pyrones is described involving the reaction of 4-hydroxy-6-methyl-2 H-pyran-2-one with aromatic aldehydes and secondary amines in the presence of oxalic acid and in aqueous media. The salient features of this protocol are aerobic conditions, short reaction times, milder reaction conditions without additives and high yields.

Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media

2014 ◽  
Vol 68 (8) ◽  
Author(s):  
Hamzeh Kiyani ◽  
Fatemeh Ghorbani
Keyword(s):  
Organic Solvent ◽  
Aqueous Media ◽  
Ethyl Cyanoacetate ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields

Abstract2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and high yields.

Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate

2017 ◽  
Vol 41 (3) ◽  
pp. 136-138 ◽  
Author(s):  
Sabereh Bougan ◽  
Alireza Hassanabadi
Keyword(s):  
Green Chemistry ◽  
Organic Solvent ◽  
Green Synthesis ◽  
Aqueous Media ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Efficient Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
High Yields

A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence of any hazardous organic solvent. Consequently, this procedure could be classified as green chemistry.

scholarly journals Three-Component One-Pot Condensation of 2-Hydroxy-1,4-Naphthoquinone with Aromatic Aldehydes and Methyl Carbamate: Synthesis of 4-aryl-3,4-Dihydronaphtho[3,4-e][1,3]Oxazine-2,5,10-Trione in Aqueous Media

2018 ◽  
Vol 42 (6) ◽  
pp. 291-293
Author(s):  
Nooshin Ghaffari-Nia ◽  
Alireza Hassanabadi
Keyword(s):  
Green Chemistry ◽  
Organic Solvent ◽  
Efficient Method ◽  
Aqueous Media ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
One Pot Condensation ◽  
Oxazine Ring ◽  
High Yields

A green and efficient method for oxazine ring formation is established using the reaction of 2-hydroxy-1,4-naphthoquinone and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydronaphtho[3,4- e][1,3] oxazine-2,5,10-triones in excellent yields. The salient features of this protocol are short reaction times and high yields while avoiding any hazardous organic solvent. Therefore, this procedure could be classified as green chemistry.

scholarly journals One-pot multi-component process for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives catalyzed by the deep eutectic solvent choline chloride-oxalic acid

2020 ◽  
Vol 75 (3) ◽  
pp. 269-279
Author(s):  
Mohammad Hosein Sayahi ◽  
Maryam Gorjizadeh ◽  
Melan Meheiseni ◽  
Soheil Sayyahi
Keyword(s):  
Oxalic Acid ◽  
Choline Chloride ◽  
Deep Eutectic Solvent ◽  
Reaction Times ◽  
Eutectic Mixture ◽  
Reaction Yield ◽  
One Pot ◽  
Experimental Procedure ◽  
Component Process ◽  
High Yields

AbstractAn effective method based on choline chloride (ChCl)-oxalic acid (Ox) deep eutectic solvent was proposed for the synthesis of 4-azaphenanthrene-3,10-dione, 1,8-dioxo-octahydroxanthene and tetrahydrobenzo[b]pyran derivatives. The eutectic mixture worked as both the solvent and acidic catalyst for conversion. The impacts of different variables, including the composition and volume of ChCl-Ox, and temperature, on reaction yield were studied for optimization. The crucial advantages of this process are simplicity of the experimental procedure, high yields, short reaction times, high recyclability, and the use of safe and inexpensive components.

One-pot multicomponent synthesis of β-acetamidoketones catalysed by pTSA1

2007 ◽  
Vol 85 (7-8) ◽  
pp. 479-482 ◽  
Author(s):  
Biswanath Das ◽  
Kongara Ravinder Reddy ◽  
Yallamalla Srinivas ◽  
Rathod Aravind Kumar
Keyword(s):  
Multicomponent Reaction ◽  
Acetyl Chloride ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
High Yields ◽  
Three Component Coupling

A catalytic amount of pTSA has been found to be effective to carry out a one-pot three-component coupling of aromatic aldehydes, enolizable ketones or ketoesters, and acetonitrile in the presence of acetyl chloride to afford β-acetamidoketones in high yields. Short reaction times and inexpensive catalyst are main advantages of this protocol.Key words: β-acetamidoketone, pTSA, multicomponent reaction, diastereoselectivity.

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.

scholarly journals An Efficient and Recycling Catalyst for the One-Pot Three-Component Synthesis of Substituted 3,4-Dihydropyrimidin-2(1H)-ones

2008 ◽  
Vol 5 (4) ◽  
pp. 688-695 ◽  
Author(s):  
Taoues Boumoud ◽  
Boudjemaa Boumoud ◽  
Salah Rhouati ◽  
Ali Belfaitah ◽  
Abdelmadjid Debache ◽  
...  
Keyword(s):  
Reaction Times ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
First Derivative ◽  
Target Molecules ◽  
The One ◽  
High Yields

The Biginelli one-pot three-component cyclocondensation was applied in this work to prepare 3,4-dihydropyrimidinone and its analogues using the first derivative of lead, Pb(NO3)2, as a recycling catalyst, from a diversity of aromatic aldehydes, β-ketoesters and urea. The reaction was carried out in refluxing acetonitrile and afforded the target molecules in good to excellent yields. The method offers several advantages including high yields of the products, short reaction times and easy experimental workup procedure

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).

scholarly journals Leucine: green and efficient catalyst for the synthesis of 4H-chromenes

2017 ◽  
Vol 10 (9) ◽  
pp. 3197-3202 ◽  
Author(s):  
Davood Azarifar ◽  
Younes Abbasi ◽  
Omolbanin Badalkhani
Keyword(s):  
Amino Acid ◽  
Condensation Reaction ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
One Pot ◽  
Efficient Catalyst ◽  
Naturally Occurring ◽  
The One ◽  
High Yields ◽  
Work Up

Leucine, a naturally occurring α-amino acid, has been found as an effective catalyst to effect the one-pot three-component condensation reaction between aromatic aldehydes, malononitrile and 5,5-dimethyl-1,3-cyclohexanedione (dimedone). Various 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile derivatives are conveniently prepared by these reactions in excellent yields. High yields, short reaction times, simple work-up, use of green and naturally occurring catalyst and solvent are the main merits of the present protocol. 

scholarly journals One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

2018 ◽  
Vol 62 (1) ◽  
Author(s):  
Jabbar Khalafy ◽  
Ramin Javahershenas
Keyword(s):  
Simple Procedure ◽  
Reaction Times ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
General Applicability ◽  
Green Approach ◽  
Three Component Reaction ◽  
High Yields ◽  
Work Up

<p>A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-<em>d</em>]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-<em>n</em>-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.</p>

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