13041-64-0Relevant academic research and scientific papers
Design, Synthesis and SAR Studies of Novel and Potent Dipeptidyl Peptidase 4 Inhibitors
Luo, Na,Fang, Xiaoyu,Su, Mingbo,Zhang, Xinwen,Li, Dan,Li, Honglin,Li, Shiliang,Zhao, Zhenjiang
supporting information, p. 115 - 120 (2020/12/28)
Dipeptidyl peptidase 4 (DPP-4) is a clinically validated target for the treatment of type 2 diabetes mellitus (T2DM). To discover novel and potent DPP-4 inhibitors, three series of compounds were designed and synthesized in this study based on our previou
Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
Chatterjee, Anamitra,K?nig, Burkhard
supporting information, p. 14289 - 14294 (2019/08/30)
The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.
Light-initiated and thermal nitration reactions during photolysis of naphthalene/tetranitromethane or 1-methoxynaphthalene/tetranitromethane in dichloromethane
Eberson, Lennart,Radner, Finn
, p. 5825 - 5834 (2007/10/02)
The photolysis of naphthalene or 1-methoxynaphthalene together with tetranitromethane in dichloromethane, using light with a cutoff at λ 2-promoted nitration (α/β ratio ca. 20). The adducts are formed by photochemical excitation of the CT complex between naphthalene and tetranitromethane, resulting in formation of the triad [ArH?+ NO2 (NO2)3C-] from which the observed chemistry develops by attack of trinitromethanide upon the radical cation. For 1-methoxynaphthalene, a representative of more highly reactive aromatics, the reaction is again photochemically initiated and again adducts seem to be responsible for the further development of thermal nitration reactions, apart from the NO2-induced reaction. Elimination of HNO2 from one of the 1,4-adducts induces a novel HNO2/tetranitromethane-dependent nitration process, shown separately to operate in the dark on reactive substrates. The aryltrinitromethane formed in this step is "hydrolyzed" to the corresponding carboxylic acid, 4-methoxy-1-naphthoic acid, under the anhydrous conditions prevailing during photolysis. Nitrous acid is a likely candidate as the proton source for this reaction. With an alcohol present, moderate yields (up to ≈50%) of alkyl 4-methoxy-1-naphthoates are obtained. From other adducts, nitro compounds are formed by elimination of nitroform. Trinitromethanide ion was shown to possess greatly differing reactivity (ratio >103) toward a model radical cation, tris(4-bromophenyl)aminium ion, in dichloromethane and acetonitrile, respectively.
Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid
Nishino, Hiroshi,Tsunoda, Katsunori,Kurosawa, Kazu
, p. 545 - 550 (2007/10/02)
The reaction of naphthlenes with malonic acid in the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids.Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products.It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl radical formed by the interaction of malonic acid and manganese(III) acetate.In addition, it was also found that the dicarboxymethyl radicals attacked the position of the highest electron density on the aromatic ring and that this formylation was effective when the ionization potential of the aromatic copound was lower than 7.8 eV.
