16807-63-9Relevant academic research and scientific papers
Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage
Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai
supporting information, p. 8389 - 8394 (2019/10/16)
C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.
Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes
Girase, Tejpalsingh Ramsingh,Kapdi, Anant R.
supporting information, p. 2611 - 2619 (2019/07/05)
A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.
Divergent Synthesis of Styryl–Cinnamate Hybrid Analogues Inspired by the Natural Product Salvianolic Acid F as a Premise To Investigate Their Anticancer Activity and Its Metabolomic Profiling
Shard, Amit,Rawat, Kiran,Sinha, Arun K.,Padwad, Yogendra,Kumar, Dinesh
supporting information, p. 5941 - 5949 (2016/12/26)
Protecting-group-free synthesis of hydroxylated styryl–cinnamate hybrids (C6–C2–C6–C3unit), inspired by the natural product salvianolic acid F, was achieved by a step-economical route involving sequential double C–C bond formation in one pot. The method involved multiple reactions (Perkin condensation/decarboxylation–Heck cross-coupling reactions) by using simple precursors (i.e., hydroxylated benzaldehyde, arylacetic acid, and acrylic acid derivatives) in one pot and yielded the desired unnatural small hybrid molecules in varying yields of 35–65 % with E selectivity under microwave irradiation, whereas the reported conventional route for the synthesis of salvianolic acid F itself requires six steps with an overall yield of 10.0 % in addition to tedious separation of E/Z isomers that arise from a Wittig reaction. Apart from an economical synthesis and product diversity, we herein report the potential of some hybrid molecules with the catechol core to selectively inhibit glioma cells. The intrinsic mode of action of our lead molecule, involving caspase 6 and the quinonemethide pathway, is also reported on the basis of1H NMR spectroscopy guided metabolomic profiling. We emphatically demonstrate the role of our hybrid molecules, analogues of salvianolic acid F, in forcing glioma cells towards apoptosis by specifically perturbing the concentration of glutathione along with that of caspase 6.
Aerobic oxidative coupling of resveratrol and its analogues by visible light using mesoporous graphitic carbon nitride (mpg-C3N4) as a bioinspired catalyst
Song, Tao,Zhou, Bo,Peng, Guang-Wei,Zhang, Qing-Bao,Wu, Li-Zhu,Liu, Qiang,Wang, Yong
supporting information, p. 678 - 682 (2014/01/23)
The first aerobic oxidative coupling of resveratrol and its analogues by mesoporous graphitic carbon nitride as a bioinspired catalyst with visible light has been developed. With this method, δ-viniferin and its analogues were synthesized in moderate to high yield. The metal-free conditions, visible-light irradiation, and the ideal oxidant, molecular oxygen, make this coupling reaction environmental friendly and practical. Copyright
Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
Chalal, Malik,Vervandier-Fasseur, Dominique,Meunier, Philippe,Cattey, Hélène,Hierso, Jean-Cyrille
, p. 3899 - 3907 (2012/07/14)
Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.
Smectic-smectic phase transitions in binary liquid-crystalline mixtures of DB5-T8
Fontes, Ernest,Lee, Wah Keat,Heiney, Paul A.,Nounesis, George,Garland, Carl W.,et al.
, p. 3917 - 3929 (2007/10/02)
We have used high-resolution x-ray diffraction and ac calorimetry to study the liquid-crystalline smectic-A-smectic-A phase transitions in binary mixtures of polar mesogenic compounds DB5 phenyl ester> and T8 ethenyl> phenyl ester>.A detailed synthesis for each of these compounds is presented.The smectic A1 phase in this system shows two collinear diffuse x-ray maxima at incommensurate wave vectors, indicating a tendency to form the predicted Ai1 phase with two strongly coupled density modulations having incommensurate wavelengths.The Ad peak position, while both temperature and concentration dependent, is remarkably constant along the N-Ad phase boundary.In the vicinity of 16 mol percent T8, both the x-ray and heat-capacity results are reproducibly history dependent.The simultaneous observation of sharp A2 and Ad peaks most likely results from phase coexistence, but a condensed incommensurate Ai2 phase cannot be ruled out.
