An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium

@article{Devi2005AnEM,
  title={An expedient method for the synthesis of 6-substituted uracils under microwave irradiation in a solvent-free medium},
  author={I. Devi and P. Bhuyan},
  journal={Tetrahedron Letters},
  year={2005},
  volume={46},
  pages={5727-5729}
}
Condensation of malonic acid 1 and ureas 2a–f proceeds smoothly in the presence of acetic anhydride 3 under microwave irradiation in solvent-free conditions to give 6-hydroxy-uracils 4 in excellent yields. Under identical conditions, the condensation of cyanoacetic acid 5 and ureas 2a,b,g and h in the presence of acetic anhydride 3, followed by cyclization in the presence of sodium hydroxide affords 6-amino-uracils 6 in high yields. The work-up procedures are simple and products need no… Expand
Ionic liquid mediated one-pot synthesis of 6-aminouracils
A novel, one-pot synthesis of 6-aminouracils via in situ generated ureas and cyanoacetylureas in the presence of an ionic liquid catalyst, 1,1,3,3-tetramethylguanidine acetate, is described. TheExpand
Microwave-assisted, solvent-free synthesis of 1-(α- or β-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction
Abstract As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol toExpand
Carboxylic acid-catalyzed one-pot synthesis of cyanoacetylureas and their cyclization to 6-aminouracils in guanidine ionic liquid
A novel, one-pot, carboxylic acid-catalyzed synthesis of cyanoacetylureas via in situ generated ureas and their cyclization to 6-aminouracils in the presence of the guanidine-based ionic liquidExpand
Preparation method of 6-chloro-1,3-dimethyluracil
The invention provides a preparation method of 6-chloro-1,3-dimethyluracil, which comprises the following steps: carry out reflux reaction on 1,3-dimethylbarbituric acid and a chlorinating agent in aExpand
A novel one-pot three-component reaction for the synthesis of 5-arylamino-pyrrolo[2,3-d]pyrimidines under microwave irradiation
Some novel 5-arylamino-pyrrolo[2,3-d]pyrimidine derivatives were synthesized via microwave-assisted three-component reaction of N,N-dimethyl-6-aminouracil, aryl glyoxal monohydrates and aryl amines.Expand
Reactions of 6‐Aminouracils: The First Simple, Fast, and Highly Efficient Synthesis of bis(6‐Aminopyrimidonyl)methanes (BAPMs) Using Thermal or Microwave‐Assisted Solvent‐Free Methods
Abstract A detailed study on the condensation reaction of 6‐aminouracils and aldehydes has been investigated, and accordingly we established for the first time two green, fast, and highly efficientExpand
Synthesis of novel 5-monoalkylbarbiturate derivatives: new access to 1,2-oxazepines
Abstract A simple and straightforward route to 5-monoalkylbarbiturates by the NHEt 2 catalyzed Michael reaction of 1,3-dimethylbarbituric acid and α,β-unsaturated ketones is described. Significantly,Expand
Ceric ammonium nitrate (CAN): an efficient and eco-friendly catalyst for the one-pot synthesis of alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methanes at room temperature
A simple, facile and convenient practical method for the one-pot synthesis of biologically relevant alkyl/aryl/heteroaryl-substituted bis(6-aminouracil-5-yl)methane scaffolds (3a–3u) has beenExpand
Synthesis of ferrocenyl-β-enamino ketones: A search of ferrocenylpyrido[2,3-d]pyrimidines using a Ni(CN)2/NaOH/KCN system as catalytic precursor
Abstract New ferrocenyl-β-enamino ketones (1–6), were obtained from 6-amino-1,3-dimethyluracil and several ferrocenyl-α-ketoalkynes via MeNH− anion in a monophasic aqueous system containingExpand
FeCl3·6H2O catalyzed aqueous media domino synthesis of 5-monoalkylbarbiturates: water as both reactant and solvent
A novel, simple and straightforward route to 5-monoalkylbarbiturates by FeCl3·6H2O catalyzed domino reactions of 6-aminouracils, water and α,β-unsaturated ketones, where water plays a key dual roleExpand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 18 REFERENCES
Sodium bromide catalysed one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component cyclocondensation under microwave irradiation and solvent free conditions
Abstract Sodium bromide catalysed three-component cyclocondensation of aryl aldehydes, alkyl nitriles and dimedone proceeds under microwave irradiation in solvent free conditions to give highlyExpand
Uracils: Versatile Starting Materials in Heterocyclic Synthesis
Publisher Summary This chapter provides a brief review on uracil and its chemistry, by no means exhaustive, has pointed out by some selective but typical examples that show uracils and theirExpand
Enantioselective Allyltitanation. Synthesis of (-)-Slaframine
An enantioselective synthesis of the indolizidine alkaloid (-)-slaframine from aldehyde 1 is reported. The stereogenic centers at C-1 and C-8a are introduced by an enantioselective allyltitanationExpand
Studies on uracils: a facile one-pot synthesis of oxazino[4,5-d]-, pyrano[2,3-d]-, pyrido[2,3-d]- and pyrimido[4,5-d]pyrimidines using microwave irradiation in the solid state
Abstract N , N -Dimethyl-5-formylbarbituric acid 1 reacts with maleimide 2 and phenyl isocyanate/phenyl isothiocyanate 4 under microwave-assisted conditions in the solid phase to afford pyrano[2,3- dExpand
Highly enantioselective approach to indolizidines: preparation of (+)-(1S,8aS)-1-hydroxyindolizidine and (-)-slaframine.
A highly stereoselective approach to (-)-slaframine and its probable biosynthetic precursor (+)-(1S,8aS)-1-hydroxyindolizidine has been developed based on a diastereofacially selective cycloadditionExpand
Comprehensive heterocyclic chemistry II
CHEC III is organized in 15 Volumes and closely follows the organization used in the previous edition: Volumes 1 and 2: Cover respectively three- and four-membered heterocycles, together with allExpand
A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine.
La synthese du compose du titre est donnee, cet analogue de nucleoside possede une activite anti-HIV-1
Zur virostatischen Wirksamkeit und zur klinischen Anwendbarkeit von 1-Allyl-3,5-diäthyl-6-chloruracil
TLDR
Investigations show that 1-allyl-3,5-diethyl-6-chlorouracil applied topically as 1% solution is efficacious in the treatment of all types of recurring herpetic skin and mucous diseases including herpes genitalis as well as stomatitis aphthosa. Expand
Analgetics based on the pyrrolidine ring.
Organic sulfur compounds
...
1
2
...