A convenient and practical method for the synthesis of 2-alkylthio-4-amino-5-cyano-6-aryl(alkyl)pyrimidines has been developed via a three-component, one-pot reaction from aldehydes, malononitrile and S-alkylisothiouronium salts in water at room temperature. A series of polysubstituted pyrimidines were prepared by this method in moderate to excellent yields. In addition, two kinds of pyrimidine-fused heterocyclic derivatives with potential pharmacological activity were constructed from our 2-alkylthio-4-amino-5-cyano-6-arylpyrimidines.
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http://dx.doi.org/10.1007/s11030-012-9376-z | DOI Listing |
Heliyon
January 2025
Department of Organic Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University, Hamedan, Iran.
This study introduces a new nano catalyst tailored for the eco-friendly synthesis of pyrido[2,3-]pyrimidine via a three-component one-pot reaction involving benzaldehydes, malononitrile, and uracil. To achieve this objective, we anchored copper acetate onto the surface of layered double hydroxides modified with 1,3‑benzenedisulfonyl amide (BDSA) (LDH@PTRMS@BDSA@Cu(NO)), which exhibited remarkable activity and selectivity. The main benefits of this method include high product yield, swift reaction times, straightforward purification, catalyst reusability, and the employment of a mild reaction process.
View Article and Find Full Text PDFOrg Lett
January 2025
China Guangxi Key Laboratory of Pharmaceutical Precision Detection and Screening, Guangxi Key Laboratory of Bioactive Molecules Research and Evaluation, and Key Laboratory of Micro-Nanoscale Bioanalysis and Drug Screening of Guangxi Education Department, Pharmaceutical College, Guangxi Medical University, Nanning 530021, China.
Herein, a one-pot domino catalyzed three-component process is described, which is initiated by a palladium/zinc cooperatively catalyzed cycloaddition between trimethylenemethane (TMM) and unactivated alkyl/aryl imines, followed by one-pot isomerization and Zn(OTf)-catalyzed DDQ oxidation, furnishing valuable substituted pyrroles. We disclose that the palladium/zinc cooperative catalysis affords a dual-Zn(OTf)-stabilized azapalladacycle, wherein the Pd-N bond is polarized by Zn(OTf), facilitating a unique outer-sphere allylic amination. Moreover, subsequent DDQ dehydrogenation can be feasibly promoted by zinc catalysis.
View Article and Find Full Text PDFChemistryOpen
January 2025
Discipline of Pharmaceutical Sciences, Catalysis and Peptide Research Unit, University of KwaZulu-Natal, Durban, 4000, South Africa.
An efficient microwave-assisted synthesis route for novel oxazolidinone analogues has been developed. The general synthesis of these compounds began with an L-proline-mediated three-component Mannich reaction between commercially available 3-fluoro-4-morpholinoaniline, aqueous formaldehyde and α-hydroxyacetone. This was followed by a one-step cyclisation to form the core structure of oxazolidinone antibiotics which was subsequently derivatized.
View Article and Find Full Text PDFMaterials (Basel)
December 2024
Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam Bin Abdulaziz University, P.O. Box 173, Al-Kharj 11942, Saudi Arabia.
This study explores a sustainable method for synthesizing quinazoline derivatives through visible light-driven photocatalysis using curcumin-sensitized titanium dioxide (TiO) nanoparticles. A one-pot, three-component reaction involving aldehydes, urea/thiourea, and dimedone was utilized to efficiently produce quinazoline compounds. The photocatalytic performance of curcumin-sensitized TiO (Cur-TiO) was compared to pure TiO (P-TiO), with Cur-TiO showing significantly enhanced activity.
View Article and Find Full Text PDFA one-pot, acid-, base-, and metal-free, multicomponent strategy has been developed to synthesize spiro thiochromene-oxindole derivatives as potential anti-inflammatory agents. The synthesized compounds were screened for their anti-inflammatory activity by inhibiting heat-induced Bovine Serum Albumin (BSA) denaturation assay, revealing moderate to good efficacy. Compounds 4e, 4k, and 4h exhibited the highest activity, inhibiting BSA denaturation by 90.
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