Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione
Nurmaganbetov Z.S. Nurkenov O.A. Fazylov S.D. Turdybekov D.M. Minayeva Y.V. Khabdolda G. Ibraybekova A.M. Tilla Z.S. Turdybekov K.M.
22 October 2024Institute of Combustion Problems, al-Farabi Kazakh State National University
Eurasian Chemico-Technological Journal
2024#26Issue 3175 - 183 pp.
The reactions of lupinine alkaloid and its chlorine derivative with cinnamoyl chloride and 2-K-isoindole-1,3-dione were investigated to obtain 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester and 2-(octahydroquinolizin-1-ylmethyl) isoindole-1,3-dione, respectively. The optimal conditions for carrying out the aforementioned reactions were determined, taking into account the nature of the solvent and medium. It was established that acylation of the molecule in a benzene medium, in the presence of trimethylamine, resulted in the formation of 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester, with an 82% yield. It was demonstrated that the interaction of chlorolupinine with 2-K-isoindole-1,3-dione under Gabriel reaction conditions resulted in the formation of 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione. The conformer with an axial orientation of the isoindole-1,3-dione substituent was observed to exhibit greater stability than the conformer with an equatorial orientation. The structure of the synthesized compounds was investigated by IR,1H, and13C NMR spectroscopy. The use of two-dimensional spectra in COSY (1H-1H) and HMQC (1H-13C) formats enabled the establishment of homo-and heteronuclear interactions, thereby confirming the structure of the compounds under investigation. The values of chemical shifts, multiplet and integrated intensity of1H and13C signals in one-dimensional NMR spectra of the novel compounds were determined. The crystal structures of 3-phenylacrylic acid octahydroquinolizin-1-ylmethyl ester and 2-(octahydroquinolizin-1-ylmethyl) isoindole-1,3-dione were elucidated through X-ray analysis.
2-(octahydroquinolizin-1-ylmethyl) isoindole-1,3-dione , 3-Phenylacrylic acid octahydroquinolizin-1-ylmethyl ester , Conformational analysis , NMR spectroscopy , X-ray analysis
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Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str. 1, Karaganda, Kazakhstan
Karaganda Medical University, Gogol str., 40, Karaganda, Kazakhstan
Karaganda Technical University, Karaganda, N. Nazarbayev str., 56, Karaganda, Kazakhstan
Karagandy Buketov University, Universitetskaya str., 28, Karaganda, Kazakhstan
Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan
Karaganda Medical University
Karaganda Technical University
Karagandy Buketov University
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