848616-40-0Relevant academic research and scientific papers
Far Away from Flatland. Synthesis and Molecular Structure of Dihetera[3.3. n]propellanes and Trihetera[3.3. n]propellanes: Advanced Analogues of Morpholine/Piperazine
Sokolenko, Yevhenii M.,Yurov, Yevhen Yu.,Vashchenko, Bohdan V.,Hryshchuk, Oleksandr V.,Filimonova, Yuliia,Ostapchuk, Eugeniy N.,Artemenko, Artem,Zaremba, Oleg V.,Grygorenko, Oleksandr O.
, p. 13908 - 13921 (2019)
An approach to di- and trihetera[3.3.n]propellanes (n = 2-4), advanced morpholine and piperazine analogues, is developed. The key step of the reaction sequence included a [3+2] cycloaddition reaction of unsaturated vicinal dicarboxylic acid derivatives and in situ generated azomethine ylide resulting in the formation of the pyrrolidine ring. One more heteroaliphatic ring (i.e., pyrrolidine or tetrahydrofuran) was annelated by nucleophilic cyclization of the appropriate 1,4-dielectrophilic intermediates. There were 11 examples of the title products obtained in 3-5 steps on a multigram scale with 10-72% overall yields. Additionally, molecular structures of homologous dihetera[3.3.n]propellanes, analogues of morpholine, were obtained from X-ray diffraction studies and analyzed using exit vector plots (EVPs). It was shown that the scaffolds obtained are somewhat larger as compared to the parent morpholine and bicyclic 3-oxa-7-azabicyclo[3.3.0]octane. Moreover, despite very similar chemical structures, they provide a very distinct spatial position of heteroatoms, which is clearly seen from the conformation adopted by a formal eight-membered ring including both N and O atoms (i.e., crown, boat-chair, twist chair-chair, and boat-boat for the oxaza[3.3.2]-, -[3.3.3]-, -[4.3.3]propellanes, and 3-oxa-7-azabicyclo[3.3.0]octane, respectively).
An Approach to 3-Oxa-7-azabicyclo[33.0]octanes - Bicyclic Morpholine Surrogates
Sokolenko, Yevhenii M.,Ostapchuk, Eugeniy N.,Artemenko, Artem,Grygorenko, Oleksandr O.
, p. 3112 - 3117 (2017/07/12)
An approach to 3-oxa-7-azabicyclo[3.3.0]octanes, bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5 H)-ones and an in situ generated azomethine ylide. The utility of the method was demonstrated on a multigram scale.
QUINOLONE ANTIBACTERIAL AGENTS
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Page/Page column 164-165, (2010/02/11)
Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.
