Probing the Reactivity of 2,4-Dichlorofuro[3,4-d]pyrimidin-7-one: A Versatile and Underexploited Scaffold to Generate Substituted or Fused Pyrimidine Derivatives

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 2010-2014
Author(s):  
Paolo Vincetti ◽  
Gabriele Costantino ◽  
Maria Grazia Martina ◽  
Marco Radi
Keyword(s):  
Chemical Reactivity ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
Microwave Assisted ◽  
Set Up

Herein, we describe the results of our investigation on the chemical reactivity and versatility of a poorly explored scaffold: 2,4-dichlorofuro[3,4-d]pyrimidin-7-one (3). Highly functionalized pyrimidines can be obtained with a divergent approach by reacting the key intermediate 3 with different amine nucleophiles under carefully controlled reaction conditions. The set-up of a microwave-assisted one-pot, two- or three-step protocol to rapidly generate 2,4,5,6-tetrasubstituted or fused pyrimidines is also reported.

scholarly journals Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

2018 ◽  
Vol 14 ◽  
pp. 1655-1659 ◽  
Author(s):  
Ugo Azzena ◽  
Massimo Carraro ◽  
Gloria Modugno ◽  
Luisa Pisano ◽  
Luigi Urtis
Keyword(s):  
Organic Chemistry ◽  
Heterogeneous Catalysis ◽  
Important Class ◽  
Green Solvents ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Acidic Catalysts ◽  
Set Up ◽  
Work Up

The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures and the versatility of the solvents allowed further conversion of the reaction products under one-pot reaction conditions.

scholarly journals Microwave Assisted Three Component Reaction Conditions to Obtain New Thiazolidinones with Different Heterocyclic Skeletons

Proceedings ◽  
2019 ◽  
Vol 41 (1) ◽  
pp. 38
Author(s):  
Fernando J. Lorenzo ◽  
Romina A. Ocampo ◽  
Sandra D. Mandolesi
Keyword(s):  
Microwave Irradiation ◽  
Thioglycolic Acid ◽  
Aldehyde Group ◽  
Green Solvent ◽  
Reaction Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Microwave Assisted ◽  
Three Component Reaction ◽  
The One

We present here a new proposal for the “one pot” generation of new 4-thiazolidinones (9a–e) through a multicomponent reaction under microwave irradiation conditions, using aromatic and heteroaromatic amines (8a–e), absolute ethanol as a “green” solvent and modifying the aldehyde group in the glycosidic residue, synthesized from D-mannitol. The study is focused in the variation of the irradiation times and the concentration of thioglycolic acid in order to study the possibility of controlling the structure and/or stereochemistry of the products formed in the reaction. Thiazolidinones 9a–d were obtained with a 69–82% The generation of the corresponding reaction products were monitored by TLC and CG-MS, taking reaction aliquots. The conditions reaction proved to be chemoselective depending on the excess of acid and irradiation times.

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.

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>

scholarly journals One-Pot Synthesis of Some New Pyrido[2,3-d]pyrimidine Derivatives Catalyzed by Sodium Lauryl Sulfate in Aqueous Media

2010 ◽  
Vol 7 (3) ◽  
pp. 779-784 ◽  
Author(s):  
Sheng-Hui Li ◽  
Yan-Hong Shen ◽  
Na Gao ◽  
Ji-Tai Li
Keyword(s):  
Aromatic Aldehyde ◽  
Sodium Lauryl Sulfate ◽  
Aqueous Media ◽  
Lauryl Sulfate ◽  
Pyrimidine Derivatives ◽  
Reaction Conditions ◽  
One Pot ◽  
Environmental Friendly ◽  
Three Component Reaction ◽  
Work Up

A series of pyrido[2,3-d]pyrimidine derivatives were synthesized by the three-component reaction of aromatic aldehyde, malononitrile and 6-amino-4-hydroxy-2-mercaptopyrimidine catalyzed by sodium lauryl sulfate (SDS) in aqueous media. It was interesting that further aromatization took place automatically. This method provides several advantages such as easier work-up, milder reaction conditions and environmental friendly.

ChemInform Abstract: An Efficient One-Pot and Solvent-Free Synthesis of Chromeno[2,3-d]pyrimidine Derivatives: Microwave Assisted Reaction.

ChemInform ◽  
2010 ◽  
Vol 41 (40) ◽  
pp. no-no
Author(s):  
Afsaneh Zonouzi ◽  
Mojtaba Biniaz ◽  
Roghieh Mirzazadeh ◽  
Merzieh Talebi ◽  
Seik Weng Ng
Keyword(s):  
Solvent Free ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Microwave Assisted ◽  
Solvent Free Synthesis

An Efficient One-Pot and Solvent-Free Synthesis of Chromeno[2,3-d]pyrimidine Derivatives: Microwave Assisted Reaction

Heterocycles ◽  
2010 ◽  
Vol 81 (5) ◽  
pp. 1271 ◽  
Author(s):  
Afsaneh Zonouzi ◽  
Mojtaba Biniaz ◽  
Roghieh Mirzazadeh ◽  
Merzieh Talebi ◽  
Seik Weng Ng
Keyword(s):  
Solvent Free ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Microwave Assisted ◽  
Solvent Free Synthesis

scholarly journals Cross-Linked Cyclodextrins Bimetallic Nanocatalysts: Applications in Microwave-Assisted Reductive Aminations

Molecules ◽  
2020 ◽  
Vol 25 (2) ◽  
pp. 410
Author(s):  
Emanuela Calcio Gaudino ◽  
Elisa Acciardo ◽  
Silvia Tabasso ◽  
Maela Manzoli ◽  
Giancarlo Cravotto ◽  
...  
Keyword(s):  
Reductive Amination ◽  
Nitro Compounds ◽  
Secondary Amines ◽  
Cross Linking ◽  
Reaction Conditions ◽  
One Pot ◽  
Microwave Assisted ◽  
Aldehydes And Ketones ◽  
Bimetallic Nanocatalysts ◽  
High Yields

The optimization of sustainable protocols for reductive amination has been a lingering challenge in green synthesis. In this context, a comparative study of different metal-loaded cross-linked cyclodextrins (CDs) were examined for the microwave (MW)-assisted reductive amination of aldehydes and ketones using either H2 or formic acid as a hydrogen source. The Pd/Cu heterogeneous nanocatalyst based on Pd (II) and Cu (I) salts embedded in a β-CD network was the most efficient in terms of yield and selectivity attained. In addition, the polymeric cross-linking avoided metal leaching, thus enhancing the process sustainability; good yields were realized using benzylamine under H2. These interesting findings were then applied to the MW-assisted one-pot synthesis of secondary amines via a tandem reductive amination of benzaldehyde with nitroaromatics under H2 pressure. The formation of a CuxPdy alloy under reaction conditions was discerned, and a synergic effect due to the cooperation between Cu and Pd has been hypothesized. During the reaction, the system worked as a bifunctional nanocatalyst wherein the Pd sites facilitate the reduction of nitro compounds, while the Cu species promote the subsequent imine hydrogenation affording structurally diverse secondary amines with high yields.

Microwave assisted one-pot synthetic route to imidazo[1,2-a]pyrimidine derivatives of imidazo/triazole clubbed pyrazole and their pharmacological screening

2018 ◽  
Vol 42 (15) ◽  
pp. 12666-12676 ◽  
Author(s):  
Pratibha Prasad ◽  
Anirudhdha G. Kalola ◽  
Manish P. Patel
Keyword(s):  
Synthetic Route ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Microwave Assisted ◽  
Pharmacological Screening ◽  
Derivatives Of

An efficient synthetic microwave-assisted, one-pot three-component condensation route for imidazo[1,2-a]pyrimidine derivatives of imidazole 4/triazole 5 clubbed pyrazole catalysed by ecofriendly base KOH.

Microwave-assisted one-pot synthesis of pyrimido［4,5-b］quinolines derivatives

2013 ◽  
Vol 30 (6) ◽  
pp. 636-642
Author(s):  
Xueli Zhang ◽  
Zhilan Lin ◽  
Huiling Hu ◽  
Jiaxin He ◽  
Yuan Gao
Keyword(s):  
One Pot ◽  
Microwave Assisted ◽  
One Pot Synthesis
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