A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1002/chem.201500210 | DOI Listing |
J Org Chem
January 2025
Center for Analysis and Synthesis, Department of Chemistry, Lund University, Lund SE 221 00, Sweden.
A diastereospecific synthesis of vicinally substituted 2-oxazolidinones from α,β-unsaturated lactams using -chloroperoxybenzoic acid is reported. Several highly substituted 2-oxazolidinones were obtained in 19-46% yields in a one-pot reaction with complete control over the relative stereochemistry. The proposed reaction sequence consists of a Baeyer-Villiger oxidation, an epoxidation, and a concerted rearrangement.
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.
View Article and Find Full Text PDFACS Omega
December 2024
SupraSelen Laboratory, Department of Chemistry, Universidade Federal Fluminense, Institute of Chemistry, Campus do Valonguinho, 24020-141 Niterói-RJ, Brazil.
Our research presents selective direct selenylation at the C-4 pyrazole ring using KSO as an oxidant under simple and mild conditions. This elegant synthesis involves the one-pot method under acidic conditions, thus minimizing reaction steps and waste generation. This innovative method allowed us to create a library of 4-selanylpyrazoles in good to excellent yields.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Applied Chemistry, Faculty of Fundamental Engineering, Nippon Institute of Technology, 4-1 Gakuendai, Miyashiro-machi, Minamisaitama-gun, Saitama 345-8501, Japan.
Stereoselective synthesis of β-fluorostyrene derivatives has been achieved. Selective isomerization of -bromofluoroalkenyl benzenes bearing various -substituents is enabled by using Ir photocatalysts with high triplet energy. Subsequent one-pot transition-metal (TM)-catalyzed reactions enable pot-economical synthesis of monofluoroalkenes in a stereoselective manner.
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.
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!