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1. Unusual Cascade Reactions of 8-Acetoxy-6-hydroxymethyllimonene with Salicylic Aldehydes: Diverse Oxygen Heterocycles from Common Precursors

   https://doi.org/10.1021/acs.joc.4c01282  

   Ilyina, Irina V; Patrusheva, Oksana S; Goltsova, Victoria V; Christopher, Kimberley M; Gatilov, Yuri V; Sidorenko, Alexander Yu; Agabekov, Vladimir E; Salakhutdinov, Nariman F; Alabugin, Igor V; Volcho, Konstantin P (August 2024, The Journal of Organic Chemistry)

   Chiral oxygen-containing heterocyclic compounds are of great interest for the development of pharmaceuticals. Monoterpenes and their derivatives are naturally abundant precursors of novel synthetic chiral oxygen-containing heterocyclic compounds. In this study, acid catalyzed reactions of salicylic aldehydes with (−)-8-acetoxy-6-hydroxymethyllimonene, readily accessible from α-pinene, leads to the formation of chiral polycyclic products of various structural types. Three of the six isolated chiral heterocyclic products obtained from salicylic aldehyde contain previously unknown polycyclic ring types. Having carried out the reaction in the presence of Brønsted or Lewis acids (Amberlyst 15, trifluoromethanesulfonic acid, trifluoroacetic acid and boron trifluoride etherate) or aluminosilicates (montmorillonite K10, halloysite nanotubes), we found that the nature of products depends on the catalyst as well as the reaction conditions (reaction time, reactant ratio, presence or absence of solvent). Detailed mechanistic insight on the complex cascade reactions for product formation is provided with extensive experimental and quantum mechanical computational studies. 

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2. Photo-and Electroluminescence from Nitrogen-Doped and Nitrogen-Sulfur Codoped Graphene Quantum Dots

   https://doi.org/10.1002/adfm.201804337  

   Hasan, Md Tanvir; Gonzalez-Rodriguez, Roberto; Ryan, Conor; Faerber, Nicolas; Coffer, Jeffery L.; Naumov, Anton V. (October 2018, Advanced Functional Materials)
3. Synthesis of Five-Membered Iodine–Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts

   https://doi.org/10.1021/acs.joc.8b01995  

   Vlasenko, Yulia A.; Postnikov, Pavel S.; Trusova, Marina E.; Shafir, Alexandr; Zhdankin, Viktor V.; Yoshimura, Akira; Yusubov, Mekhman S. (September 2018, The Journal of Organic Chemistry)
4. Probing the Reversible Binding of Anionic Reactive Sulfur and Nitrogen Species in Imidazolium Receptors with Directional C–H Hydrogen Bonds

   https://doi.org/10.1021/acs.inorgchem.5c00821  

   Davis, Amanda G; Zakharov, Lev N; Pluth, Michael D (April 2025, Inorganic Chemistry)
5. Controlling Tautomerization in Pyridine‐Fused Phosphorus‐Nitrogen Heterocycles

   https://doi.org/10.1002/chem.202200472  

   McNeill, J_Nolan; Karas, Lucas_J; Bard, Jeremy_P; Fabrizio, Kevin; Zakharov, Lev_N; MacMillan, Samantha_N; Brozek, Carl_K; Wu, Judy_I; Johnson, Darren_W; Haley, Michael_M (March 2022, Chemistry – A European Journal)

   Abstract Inclusion of a second nitrogen atom in the aromatic core of phosphorus‐nitrogen (PN) heterocycles results in unexpected tautomerization to a nonaromatic form. This tautomerization, initially observed in the solid state through X‐ray crystallography, is also explained by computational analysis. We prepared an electron deficient analogue (2 e) with a fluorine on the pyridine ring and showed that the weakly basic pyridine resisted tautomerization, providing key insights to why the transformation occurs. To study the difference in solution vs. solid‐state heterocycles, alkylated analogues that lock in the quinoidal tautomer were synthesized and their different¹H NMR and UV/Vis spectra studied. Ultimately, we determined that all heterocycles are the aromatic tautomer in solution and all but2 eswitch to the quinoidal tautomer in the solid state. Better understanding of this transformation and under what circumstances it occurs suggest future use in a switchable on/off hydrogen‐bond‐directed receptor that can be tuned for complementary hydrogen bonding. 

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