Benzoic acid and benzyl alcohol are the most used raw materials in cosmetics and pharmaceutical industries as preservative ingredients. Cinnamon cassia oil is an important natural starting material to synthesize organic compounds because it contains a high amount of cinnamaldehyde and benzaldehyde. Thanks to green chemistry techniques using mild solvents such as water and ethanol, as well as low-cost and safe reagents such as potassium permanganate, and sodium borohydride, this natural starting material was used to synthesize high yields of benzoic acid, benzyl alcohol, cinnamyl alcohol, phenylpropanol, and cinnamic acid; these products are used in cosmetics, pharmaceutical, and food industries. Various reaction conditions were applied to find convenient green chemistry procedures. Equivalents (molar) of catalysts to starting materials were optimized. The highest yields (60–90%) were achieved using water as a solvent, potassium permanganate as an oxidation catalyst, and sodium borohydride as a reduction catalyst. Water was used as a solvent in all reactions except phenylpropanol. The uses of a single natural starting material, water as a solvent, and mild reagents to synthesize five important organic compounds are all in line with green chemistry techniques.

Six 9-thienyl-10-aryl-substituted 3,3,6,6-tetramethyl-decahydroacridine-1,8-diones (5a–f) were prepared by two acid-mediated routes that used the same solvent, temperature, and reaction time. In the sequential route, preformed 5,5-dimethyl-3-(arylamino)cyclohex-2-enones were reacted with a heteroaryl aldehyde and dimedone; in the corresponding one-pot route, the arylamine, heteroaryl aldehyde, and two equivalents of dimedone were combined directly. The isolated yields of the product-forming second stage were 71–75%, corresponding to calculated overall two-step yields of 58.2–68.6% after accounting for the isolated enaminone-preparation yields. These overall yields remained higher than those of the one-pot procedure (40–47%), although the sequential protocol required an additional reaction, isolation, catalyst charge, and solvent-intensive operation. Structural assignments were based on the available IR, ¹H NMR, ¹³C NMR, and EI-MS data. Tetrahydroacridinone by-products 6a–c were isolated in 13–15% yields and showed diagnostic spectral changes relative to 5a–f, including loss of the C-9 methine resonance and appearance of a strongly deshielded aromatic proton at 9.17–9.21 ppm. Within the limitations of an operational preparative comparison, the product distribution is consistent with a sequence-control interpretation in which preformation of the β-enaminone favors the 1:1:2 aldehyde/amine/dimedone product, whereas simultaneous component activation permits competing Knoevenagel, xanthene-forming, and aromatization pathways. This study provides a practical synthesis of thienyl-substituted decahydroacridine-1,8-diones and a mechanistically cautious explanation for the reduced selectivity of the one-pot process.

Mannose triflate is an established precursor for nucleophilic 2-deoxy-2-[¹⁸F]fluoro-D-glucose ([¹⁸F]FDG) production, but same-scale, stage-resolved process behavior is incompletely documented. This retrospective study combines three 100 g D-mannose confirmation batches with exploratory process-deviation observations. Stage III (orthoester isolation), Stage IV (selective hydrolysis), and Stage V (triflation) showed recorded yield relative standard deviations (RSDs) of 9.7%, 14.5%, and 2.0%, respectively. Recovery of contemporaneous process-validation and research and development (R&D) records provided direct batch-specific Stage III outputs and Stage IV/V charges and outputs, resolving the principal yield-denominator ambiguity; one archived Stage IV-to-V carry-forward mismatch in MT-09.06.004 remains explicitly unresolved. Elevated Stage IV evaporation temperature (20/36 °C versus ≤12–13 °C) produced an additional component on thin-layer chromatography (TLC) and was followed by a 15-peak gas chromatography (GC) mixture; shortened Stage II bromination and hexane-only Stage III isolation were also associated with poorer downstream outcomes. A single Stage VI dichloromethane/cyclohexane trial recovered 31.36 g from 34.0 g (92.2% rounded). Three later batches showed 97.6–98.1% high-performance liquid chromatography (HPLC) assay and 0.07–0.12% total impurities. One nonclinical radiosynthesis showed that the synthesized precursor underwent nucleophilic [¹⁸F]fluorination (69.4% decay-corrected yield; 99.7% radio-HPLC area); no in vivo validation was performed. The principal contribution is a stage-resolved map of process sensitivity rather than a new synthetic route or a validated good manufacturing practice (GMP) process.

Aims and Objective: Condensation of 5-hetarylidene-2,2-dimethyl-1,3-dioxane-4,6-diones with 5,5-dimethyl-3-arylamino-2-cyclohexanones yields 1-aryl-4-hetaryl-7,7-dimethyl-2,5-dioxo-l,2,3,4,5,5,7,8-octahydro-quinolines. The structures of all the synthesized compounds have been verified by IR, 1H-NMR, 13C-NMR, and mass spectral methods. The 13C-NMR assignments were supported by HSQC and HMBC experiments. Moreover, spin decoupling and NOE experiments have been carried out in order to elucidate stereoisomeric configurations of the compounds. It has been established that the N-phenyl ring, which projects from the plane of the octahydroquinolinedione ring, has a shielding effect on the magnetic field of the protons at 7- and 8-positions of the ring in the molecules of the compounds synthesized.Materials and Methods: The NMR spectra were recorded on a Varian Gemini spectrometer [400 MHz (1H) and 100 MHz (13C)]. EI mass spectra were obtained with a Hewlett Packard GC/MS 6890/5973 machine. MALDI-TOF mass measurements were recorded on a Bruker auto-flex III smart beam.Results: Various reaction conditions were applied in order to find an optimum and convenient procedure for the formation of octahydroquinoline derivates having hetaryl group. The highest yields (40-50 %) were achieved using acetic acid as solvent, p-toluenesulphonic acid as acidic catalyst, and excess enaminone (1.5 equiv).Conclusion: We synthesized eight new 1-aryl-7,7-dimethyl-4-hetaryl-1,2,3,4,5,6,7,8-octahydro-quinoline-2,5-dione compounds containing thienyl core as a result of Michael addition reaction of Knoevenagel products of Meldrum’s acid with dimedone enaminone compounds. Optimum circumstances were established using various reaction conditions and catalyzers throughout the research. The structures of all the synthesized compounds were analyzed by IR, 1H-NMR, 13C-NMR, and mass spectral methods. Furthermore, the structures were verified with the help of 2D (HSQC and HMBC), spin decoupling, and NOE NMR techniques.

Salicylic acid is widely used in dermatological and cosmetic formulations, yet the influence of its production route on solid-state structure and biological behaviour remains underexplored. This study compares a naturally derived salicylic acid (NSA), obtained from wintergreen oil through green chemistry, with a synthetic form (SSA) produced via the Kolbe–Schmitt reaction, integrating physicochemical characterization with antioxidant and immunomodulatory profiling. Crystal morphology, crystallinity (XRD, FTIR), melting point, solubility, dissolution and Franz-cell skin permeation were determined, alongside intrinsic radical scavenging (DPPH), intracellular reactive oxygen species (DCFH-DA), cytoprotection (MTT), CD9⁺ extracellular-vesicle (EV) release and cytokine transcription in RAW 264.7 macrophages. SSA formed uniform, needle-like crystals of higher crystallinity, comparable equilibrium solubility (2.239 vs. 2.115 mg/mL; not significant) and faster dissolution, whereas the less-ordered NSA showed a numerically higher steady-state flux (39.94 ± 16.43 µg cm⁻² h⁻¹) and a shorter lag time (2.47 ± 1.71 h). SSA was the stronger radical scavenger (DPPH 20.7% vs. 8.7%) and reduced intracellular ROS more effectively, while NSA afforded greater cytoprotection. Both forms were associated with a lower CD9⁺ EV concentration in the conditioned medium following LPS stimulation, with SSA consistently more active across radical scavenging, ROS and vesicle endpoints. These findings show that the synthesis route, through its effect on solid-state properties, influences the physical performance, while the biological behaviour is discussed separately from the anti-inflammatory behaviour of salicylic acid, informing the rational selection of natural versus synthetic material for topical applications.