Murrayaquinones A-D is a group of four bioactive carbazole-1,4-dione natural products isolated from the root bark of the plant hayata. Murrayaquinone is synthesized in five steps starting from the commercially available 2,4,5-trimethoxybenzaldehyde with an overall yield of 45%. The novelty of this murrayaquinone synthesis is in the use of a Mn(OAc) mediated oxidative radical reaction of a N-benzylaminoquinone derivative with 2-cyclohexen-1-one for the late-stage indole ring construction.
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http://dx.doi.org/10.1016/j.tetlet.2018.01.007 | DOI Listing |
Langmuir
January 2025
Department of Chemical Engineering, Canakkale Onsekiz Mart University,17100 Canakkale, Turkey.
Radioactive iodine, a key waste product of nuclear energy, has been a significant concern among nuclear materials because of its high volatility and its ability to easily enter the human metabolism. Porous materials containing a large number of N-heterocyclic units such as carbazole in the skeletons use as effective adsorbents showing high iodine capture capacities. Herein, a new carbazole-bismaleimide-based hyper-cross-linked porous organic polymer (CzBMI-POP) was successfully prepared from a new tetra-armed carbazole-maleimide monomer (Bis-Cz(BMI)), which contains biscarbazole units and maleimide side groups.
View Article and Find Full Text PDFJ Org Chem
January 2025
Peptide Chemistry Research Institute, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran 19697-64499, Iran.
Herein, we disclose a novel, mild, transition-metal-free approach to synthesizing diversely functionalized isothiocyanates from the corresponding isocyanide precursors, achieving high to excellent yields (up to 97%). The current method sheds light on the reactivity of pyridinium 1,4-zwitterionic thiolates as an unprecedented sulfur source strikingly distinct from their previously known reactivity in ionic annulation reactions, showcasing an innovative approach to organic synthesis.
View Article and Find Full Text PDFJ Chem Inf Model
January 2025
Theoretical Division, Los Alamos National Laboratory, Los Alamos, New Mexico 87545, United States.
In the field of computational chemistry, predicting bond dissociation energies (BDEs) presents well-known challenges, particularly due to the multireference character of reactive systems. Many chemical reactions involve configurations where single-reference methods fall short, as the electronic structure can significantly change during bond breaking. As generating training data for partially broken bonds is a challenging task, even state-of-the-art reactive machine learning interatomic potentials (MLIPs) often fail to predict reliable BDEs and smooth dissociation curves.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450052, China.
We present a visible-light-promoted radical cascade cyclization reaction sulfonylmethylation, cyano insertion, and radical cyclization of unactivated alkenes bearing cyano groups. This strategy enables the rapid synthesis of sulfonylmethylated phenanthridines under mild conditions with broad substrate compatibility, operational simplicity, and mild reaction conditions. The developed approach provides a novel pathway for assembling complex polycyclic nitrogen-containing frameworks, addressing a critical synthetic challenge and expanding the toolbox of photochemical transformations in organic synthesis.
View Article and Find Full Text PDFJ Phys Chem Lett
January 2025
Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200433, China.
The photochemistry of nitrous acid (HONO) plays a crucial role in atmospheric chemistry as it serves as a key source of hydroxyl radicals (OH) in the atmosphere; however, our comprehension of the underlying mechanism for the photochemistry of HONO especially in the presence of water is far from being complete as the transient intermediates in the photoreactions have not been observed. Herein, we report the photochemistry of microsolvated HONO by water in a cryogenic N matrix. Specifically, the 1:1 hydrogen-bonded water complex of HONO was facially prepared in the matrix through stepwise photolytic O oxidation of the water complex of imidogen (NH-HO) via the intermediacy of the elusive water complex of peroxyl isomer HNOO.
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