Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione
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 fo...
Saved in:
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
al-Farabi Kazakh National University
2024-10-01
|
| Series: | Eurasian Chemico-Technological Journal |
| Subjects: | |
| Online Access: | https://ect-journal.kz/index.php/ectj/article/view/1641 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832582507778801664 |
|---|---|
| author | Zh.S. Nurmaganbetov O.A. Nurkenov S.D. Fazylov D.M. Turdybekov Ye.V. Minayeva G. Khabdolda A.M. Ibraybekova Zh.S. Tilla K.M. Turdybekov |
| author_facet | Zh.S. Nurmaganbetov O.A. Nurkenov S.D. Fazylov D.M. Turdybekov Ye.V. Minayeva G. Khabdolda A.M. Ibraybekova Zh.S. Tilla K.M. Turdybekov |
| author_sort | Zh.S. Nurmaganbetov |
| collection | DOAJ |
| description |
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, and 13C 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 of 1H and 13C 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.
|
| format | Article |
| id | doaj-art-491e01930e53454a9be2bd821d86beab |
| institution | Kabale University |
| issn | 1562-3920 2522-4867 |
| language | English |
| publishDate | 2024-10-01 |
| publisher | al-Farabi Kazakh National University |
| record_format | Article |
| series | Eurasian Chemico-Technological Journal |
| spelling | doaj-art-491e01930e53454a9be2bd821d86beab2025-01-29T15:42:09Zengal-Farabi Kazakh National UniversityEurasian Chemico-Technological Journal1562-39202522-48672024-10-0126310.18321/ectj1641Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-DioneZh.S. Nurmaganbetov0O.A. Nurkenov1S.D. Fazylov2D.M. Turdybekov3Ye.V. Minayeva4G. Khabdolda5A.M. Ibraybekova6Zh.S. Tilla7K.M. Turdybekov8Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str. 1, Karaganda, Kazakhstan; Karaganda Medical University, Gogol str., 40, Karaganda, KazakhstanInstitute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str. 1, Karaganda, KazakhstanInstitute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan, Alikhanov str. 1, Karaganda, KazakhstanKaraganda Technical University, Karaganda, N. Nazarbayev str., 56, Karaganda, KazakhstanKaragandy Buketov University, Universitetskaya str., 28, Karaganda, KazakhstanKaraganda Medical University, Gogol str., 40, Karaganda, KazakhstanKaraganda Medical University, Gogol str., 40, Karaganda, KazakhstanKaraganda Medical University, Gogol str., 40, Karaganda, KazakhstanKaragandy Buketov University, Universitetskaya str., 28, Karaganda, Kazakhstan 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, and 13C 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 of 1H and 13C 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. https://ect-journal.kz/index.php/ectj/article/view/16413-Phenylacrylic acid octahydroquinolizin-1-ylmethyl ester, 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione, NMR spectroscopy, X-ray analysis, conformational analysis |
| spellingShingle | Zh.S. Nurmaganbetov O.A. Nurkenov S.D. Fazylov D.M. Turdybekov Ye.V. Minayeva G. Khabdolda A.M. Ibraybekova Zh.S. Tilla K.M. Turdybekov Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione Eurasian Chemico-Technological Journal 3-Phenylacrylic acid octahydroquinolizin-1-ylmethyl ester, 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione, NMR spectroscopy, X-ray analysis, conformational analysis |
| title | Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione |
| title_full | Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione |
| title_fullStr | Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione |
| title_full_unstemmed | Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione |
| title_short | Synthesis and Spatial Structure of 3-Phenylacrylic Acid Octahydroquinolizin-1-Ylmethyl Ester and 2-(Octahydroquinolizin-1-Ylmethyl)Isoindole-1,3-Dione |
| title_sort | synthesis and spatial structure of 3 phenylacrylic acid octahydroquinolizin 1 ylmethyl ester and 2 octahydroquinolizin 1 ylmethyl isoindole 1 3 dione |
| topic | 3-Phenylacrylic acid octahydroquinolizin-1-ylmethyl ester, 2-(octahydroquinolizin-1-ylmethyl)isoindole-1,3-dione, NMR spectroscopy, X-ray analysis, conformational analysis |
| url | https://ect-journal.kz/index.php/ectj/article/view/1641 |
| work_keys_str_mv | AT zhsnurmaganbetov synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT oanurkenov synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT sdfazylov synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT dmturdybekov synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT yevminayeva synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT gkhabdolda synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT amibraybekova synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT zhstilla synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione AT kmturdybekov synthesisandspatialstructureof3phenylacrylicacidoctahydroquinolizin1ylmethylesterand2octahydroquinolizin1ylmethylisoindole13dione |