scholarly journals Synthesis of substituted pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines in the one-pot condensation of 2-thio-6-aminouracil, arylglyoxals and CH-acids

2019 ◽  
Keyword(s):  
Acetoacetic Ester ◽  
Phenacyl Bromide ◽  
Unsaturated Ketone ◽  
Activity Profile ◽  
One Pot ◽  
Ch Acids ◽  
One Pot Condensation ◽  
The One ◽  
Phenacyl Derivatives ◽  
Derivatives Of

We have developed some available and effective methods for the synthesis of substituted pyrrolo[2,3-d]pyrimidines and 5,8-dihydropyrido[2,3-d]pyrimidines based on the three-component condensation of 6-amino-2-thiouracil with arylglyoxal hydrates and N,N-dimethylbarbituric acid or acyclic β-dicarbonyl compounds: acetylacetone (acetoacetic ester). It was shown that the optimal product yields were obtained by boiling the reagents in acetic acid. Thus, the synthesis of pyrrolo[2,3-d]pyrimidines took 15-20 minutes, while the precipitation of 5,8‑dihydropyrido[2,3-d]pyrimidines formed only after 2 hours. We proposed possible mechanisms for the formation of anelated pyrrole and pyridine rings. In both cases, the reaction includes the formation of an intermediate of α,β-unsaturated ketone with the participation of arylglyoxal and CH-acid (N,N-dimethylbarbituric or acetylacetone (acetoacetic ester)), nucleophilic addition of 6-aminothiouracil via an activated double bond, condensation of carbonyl and amino groups. The formation of the cycle takes place exclusively with the participation of the acetyl moiety, while the pyrrol one forms during the condensation of the aroyl moiety and the 6-amino group of thiouracil. A series of synthesized pyrrolo[2,3-d]pyrimidines was modified by alkylation. As it was expected, alkylation proceeds at the sulfur atom, that allowed a significant increase in the solubility of the obtained products. The reaction was carried out in DMF by stirring the initial reagents at 60ºC (reaction with methyl iodide) or boiling them (alkylation with phenacyl bromide), whereby S-methyl and S-phenacyl derivatives of pyrrolo[2,3-d]pyrimidines were obtained. The spectral data of 1H NMR showed that S-methylation products form solvates with DMF as 1:1. The synthesized compounds can become the basis to create small libraries of anelated pyrimidines with improved antiviral activity profile.

A new more atom-efficient multi-component approach to tetrasubstituted imidazoles: one-pot condensation of nitriles, amines and benzoin

RSC Advances ◽  
2016 ◽  
Vol 6 (71) ◽  
pp. 67281-67289 ◽  
Author(s):  
Ali Khalafi-Nezhad ◽  
Mohsen Shekouhy ◽  
Hashem Sharghi ◽  
Jasem Aboonajmi ◽  
Abdolkarim Zare
Keyword(s):  
Primary Amines ◽  
One Pot ◽  
One Pot Condensation ◽  
Component Approach ◽  
The One ◽  
Tetrasubstituted Imidazoles

A new more atom-efficient multi-component approach for the synthesis of tetrasubstituted imidazoles via the one-pot condensation of nitriles, primary amines and benzoin has been described.

Magnesium Perchlorate Catalyzed Phospha-Michael Addition of Dialkyl Phosphite to Chalcone

2018 ◽  
Vol 15 (7) ◽  
pp. 1020-1023 ◽  
Author(s):  
Adarsh Sahu ◽  
Shweta Mishra ◽  
Asmita Gajbhiye ◽  
Ram Kishore Agrawal
Keyword(s):  
Bond Formation ◽  
Solvent Free ◽  
Diethyl Phosphite ◽  
Unsaturated Ketone ◽  
Dialkyl Phosphite ◽  
Magnesium Perchlorate ◽  
One Pot ◽  
Free Condition ◽  
Solvent Free Condition ◽  
Derivatives Of

Aim and Objective: Phosphonate possesses a broad range of applications ranging from agrochemistry to medicines. Because of the synthetic and biological importance of phosphonate, their chemistry has stimulated an increasing interest. Hence we developed an efficient and eco-friendly Mg(ClO4)2 catalyzed one pot, solvent free synthesis of phosphonate derivatives of chalcones. Materials and Methods: Magnesium perchlorate phosphonate derivatives of chalcones were synthesized. The reactions were executed at room temperature in the presence of Anhydrous Magnesium perchlorate Anhy. Mg(ClO4)2 under solvent free condition, affording high yield of the product. The cardinal significance of the method lies in its uncomplicated and eco- friendly experimental conditions. Results: The PMA method for P-C bond formation, using dialkyl phosphite with chalcone, was performed in the presence of Anhydrous Magnesium perchlorate under solvent free condition. Despite the solvent free condition, the methodology is efficient since it is required only in catalytic amount of Anhy. Mg(ClO4)2 in one pot reaction. Results demonstrated that the catalytic PMA of dimethyl phosphite, diethyl phosphite, diisopropyl phosphite and dibutyl phosphite with chalcone generates desired products with a percentage yield of 60-80%. Conclusion: We have developed a new efficient PMA method for P-C bond formation, using dialkyl phosphite with α,β-unsaturated ketone i.e. chalcone. To the best of our knowledge, Anhy. Mg(ClO4)2 catalyzed phosphamicheal addition of dialkyl phosphite with chalcones was found to be a new and efficient method for various biological applications.

scholarly journals Zr(HSO4)4: An Efficient Catalyst for the Synthesis of 3-(2'- Benzothiazolyl)-2,3-dihydroquinazolin- 4(1H)-ones

2012 ◽  
Vol 9 (2) ◽  
pp. 739-743 ◽  
Author(s):  
Liqiang Wu
Keyword(s):  
Solvent Free ◽  
Isatoic Anhydride ◽  
Efficient Synthesis ◽  
One Pot ◽  
Efficient Catalyst ◽  
Solvent Free Conditions ◽  
One Pot Condensation ◽  
The One

A simple and efficient synthesis of 3-(2'-benzothiazolyl)-2,3-dihydro quinazolin-4(1H)- ones has been accomplished by the one-pot condensation of isatoic anhydride, aldehyde and 2-aminobenzothiazole under solvent-free conditions in the presence of Zr(HSO4)4.

scholarly journals Efficient synthetic protocols for the preparation of common N-heterocyclic carbene precursors

2015 ◽  
Vol 11 ◽  
pp. 2318-2325 ◽  
Author(s):  
Morgan Hans ◽  
Jan Lorkowski ◽  
Albert Demonceau ◽  
Lionel Delaude
Keyword(s):  
Microwave Irradiation ◽  
Triethyl Orthoformate ◽  
Critical Assembly ◽  
Efficient Synthesis ◽  
Imidazolium Chloride ◽  
One Pot ◽  
Additional Step ◽  
One Pot Condensation ◽  
The One ◽  
Imidazolinium Salts

The one-pot condensation of glyoxal, two equivalents of cyclohexylamine, and paraformaldehyde in the presence of aqueous HBF4 provided a straightforward access to 1,3-dicyclohexylimidazolium tetrafluoroborate (ICy·HBF4). 1,3-Dibenzylimidazolium tetrafluoroborate (IBn·HBF4) was obtained along the same lines. To synthesize 1,3-diarylmidazolium salts, it was necessary to isolate the intermediate N,N'-diarylethylenediimines prior to their cyclization. Although this additional step required more time and reagents, it led to a much more efficient overall process. It also proved very convenient to carry out the synthesis of imidazolinium salts in parallel to their imidazolium counterparts via the reduction of the diimines into diammonium salts. The critical assembly of the C2 precarbenic unit was best achieved with paraformaldehyde and chlorotrimethylsilane in the case of imidazolium derivatives, whereas the use of triethyl orthoformate under microwave irradiation was most appropriate for the fast and efficient synthesis of imidazolinium salts. This strategy was applied to the synthesis of six common N-heterocyclic carbene precursors, namely, 1,3-dimesitylimidazolium chloride (IMes·HCl), 1,3-dimesitylimidazolium tetrafluoroborate (IMes·HBF4), 1,3-dimesitylimidazolinium chloride (SIMes·HCl), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IDip·HCl or IPr·HCl), 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride (SIDip·HCl or SIPr·HCl), and 1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)imidazolium chloride (IDip*·HCl or IPr*·HCl).

Synthesis of Novel Derivatives of (Benz)Imidazo[2,1-b]Pyrimido[4,5-d][1,3]Thiazine

2017 ◽  
Vol 41 (12) ◽  
pp. 730-733 ◽  
Author(s):  
Marzieh Akbarzadeh ◽  
Mehdi Bakavoli ◽  
Hossein Eshghi ◽  
Ali Shiri
Keyword(s):  
Secondary Amines ◽  
The Novel ◽  
One Pot ◽  
The One ◽  
Derivatives Of

Several derivatives of the novel heterocyclic systems 2-substituted-imidazo- and benzimidazo-[2,1- b]pyrimido[4,5- d][1,3]thiazine have been synthesised through the one-pot cyclocondensation of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine with imidazolidine-2-thione and 1 H-benzimidazole-2(3 H)-thione and subsequently substituted by various secondary amines in moderately good yields.

scholarly journals One-Pot Synthesis of B-Aryl Carboranes with Sensitive Functional Groups Using Sequential Cobalt- and Palladium-Catalyzed Reactions

Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1348
Author(s):  
Sergey A. Anufriev ◽  
Akim V. Shmal’ko ◽  
Kyrill Yu. Suponitsky ◽  
Igor B. Sivaev
Keyword(s):  
Functional Groups ◽  
X Ray Diffraction ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions ◽  
The One ◽  
Solid State Structures ◽  
Derivatives Of

The simple and efficient method was developed for the one-pot synthesis of B-substituted aryl derivatives of ortho-carborane with functional groups sensitive to organolithium and organomagnesium reagents using 9-iodo-ortho-carborane and generated in situ organozinc compounds. The method proposed was used to prepare a series of 9-aryl-ortho-carboranes, including those containing nitrile and ester groups, 9-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, o-OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, and p-COOEt). It was demonstrated that the same approach can be used for synthesis of diaryl derivatives of ortho-carborane 9,12-(RC6H4)2-1,2-C2B10H10 (R = H, p-Me). The solid-state structures of 9-RC6H4-1,2-C2B10H11 (R = p-NMe2, p-OCH2OMe, o-OMe, o-CN, p-CN, m-COOEt, and p-COOEt) and 9,12-(p-MeC6H4)2-1,2-C2B10H10 were determined by single crystal X-ray diffraction.

One-pot synthesis of β-amino carbonyl compounds catalyzed silica supported phenylphosphinic acid

2015 ◽  
Vol 4 (1) ◽  
Author(s):  
Di Liu ◽  
Jingwei Zhang ◽  
Chi Zhang ◽  
Xiaoyan Kou
Keyword(s):  
Cost Efficiency ◽  
Carbonyl Compounds ◽  
Aromatic Aldehydes ◽  
Reusable Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Environment Friendly ◽  
Aliphatic Ketones ◽  
One Pot Condensation ◽  
The One

AbstractA simple and facile synthesis of β-amino carbonyl compounds was developed by the one-pot condensation of cyclohexanone, aromatic aldehydes and anilines at 25°C in the presence of silica supported phenylphosphinic acid. β-Amino carbonyl compounds were obtained in moderate to good yields and reasonable diastereoselectivities. This method has the advantages of short reaction time, mild reaction conditions, reusable catalyst, cost efficiency and environment friendly. In addition, acetophenone and aliphatic ketones as reactants were investigated.

Eco-Friendly Synthesis of 2-Substituted Benzimidazoles Using Air as the Oxidant

2013 ◽  
Vol 66 (2) ◽  
pp. 262 ◽  
Author(s):  
Guo-Feng Chen ◽  
Hai-Dong Shen ◽  
Hui-Ming Jia ◽  
Li-Yan Zhang ◽  
Hong-Yan Kang ◽  
...  
Keyword(s):  
Room Temperature ◽  
Environmentally Friendly ◽  
Aromatic Aldehydes ◽  
Absolute Ethanol ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Condensation ◽  
The One

A simple, environmentally friendly procedure for the synthesis of 2-substituted benzimidazoles by the one-pot condensation of o-phenylenediamines with aromatic aldehydes using continuous bubbling of air in absolute ethanol at room temperature is described. The simplicity of the system, mild conditions, involvement of a non-toxic and practically inexhaustible oxidant, easy and quick isolation of the products, and moderate to good yields are the main advantages of this procedure.

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