The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.
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Chem Biodivers
January 2025
Taibah University, Chemistry, Um alqara, Alula, SAUDI ARABIA.
In the current study, new pyranopyrazole analogues (9a-d and 10a-d) were synthesized through a one-pot condensation reaction of 2-arylacetohydrazide. The inhibitory abilities were investigated against the XO enzyme through experimental and molecular docking analyses. The synthesis studies were based on ultrasound-mediated condensation reactions of four-component systems containing 2-arylacetohydrazide, ethyl acetoacetate, indoline-2,3-dione, and ethyl 2-cyanoacetate/malononitrile in various solvents and catalysts to yield pyranopyrazole analogues (9a-d and 10a-d) in a short reaction time and remarkably favorable yields ranging from 79-92%.
View Article and Find Full Text PDFCurr Pharm Des
January 2025
Institute of Materials Research, Tsinghua Shenzhen International Graduate School (SIGS), Tsinghua University, Shenzhen 518055, China.
Introduction: An efficient and four-component one-pot facile synthesis of tetra-substituted imidazole is achieved by cyclo-condensation reaction of benzil with subsequent successive substitution of aromatic aldehydes, ester substituted amine and ammonium acetate via refluxing the mixture for almost two hours at 140°C.
Method: The ending point of the understudy reaction was examined by TLC after regular intervals. Synthesized 1,2,4-tetrasubstituted imidazoles were characterized by physical data and the structural features were analyzed using spectroscopic techniques such as FTIR, NMR and elemental analysis.
ACS Nano
December 2024
Key Laboratory of Clinical Laboratory Diagnosis and Translational Research of Zhejiang Province, Translational Medicine Laboratory, The First Affiliated Hospital of Wenzhou Medical University institution, Wenzhou, Zhejiang 325035, China.
Periodontitis is characterized by dysbiotic biofilms, gingival inflammation, and bone resorption, highlighting the urgent need for a comprehensive approach to drug combination therapy. In this study, we introduce dynamic covalent nanonetworks (dcNNWs) synthesized through a one-pot, four-component reaction-induced self-assembly method using polyamines, 2-formylphenylboronic acid, epigallocatechin gallate, and alendronate. The formation of iminoboronate bonds drives the creation of dcNNWs, allowing controlled release in the periodontitis microenvironment.
View Article and Find Full Text PDFJ Org Chem
November 2024
School of Chemistry, University of Hyderabad, P.O. Central University, Gachibowli, Hyderabad 500046, India.
Herein, we report an atom-economical, one-pot, four-component, diastereoselective double-annulation reaction to construct polyfused pyrroloquinolines. This reaction highlights the cyclization of in situformed Povarov adducts with allenoates for the first time.
View Article and Find Full Text PDFJ Org Chem
November 2024
State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China.
The synthesis of multifunctionalized dihydropyridinones from aldehydes and ketones involves at least a three-step process, making route shortening a challenging task, especially in achieving a one-pot four-component synthesis via aldehydes and ketones precondensation. Herein, we discovered a [1 + 2 + 1 + 2] four-component domino cyclization reaction, a novel concept in 4CRs with commercially available ketones and aldehydes, which by initially combining aldehydes and ketones with Meldrum's acid and ammonium acetate (NHOAc), respectively, they give dihydropyridones (>110 examples). This transformation features inexpensive additives and readily available starting materials, making it appropriate for rapid access to relevant pharmaceutical molecules containing dihydropyridinone-derived heterocycles.
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