The preparation of N-alkyl acyclic imides
Apstrakt
An optimized method for the preparation of a little known class of compounds, acyclic imides, is described. First, the N-metalation of selected secondary am des was examined, using various bases and solvents. The most efficient metalating agent was found to be butyllithium in tetrahydrofuran. The N-lithiated amides were then acylated at -60 °C, with an acid chloride or anhydride to afford the corresponding acyclic imide in high yields. A total of 14 acyclic imides were prepared in this manner, most of them being new compounds. Among the two workup procedures examined, aqueous and nonaqueous, the latter was found to be more efficient. Compared to the literature procedures, this novel method appears to be superior in yields, purity and the time required for the preparaton. In view of the fact that acyclic imides are considerably reactive, they may become useful intermediates in synthesis.
Ključne reči:
Acyclic imides / N-metalationIzvor:
Journal of the Serbian Chemical Society, 1996, 61, 2, 69-76Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Mićović, I.V. AU - Ivanović, Milovan AU - Lečić, V.M. AU - Roglić, Goran AU - Kiricojević, V.D. AU - Popović, J.B. PY - 1996 UR - https://cherry.chem.bg.ac.rs/handle/123456789/54 AB - An optimized method for the preparation of a little known class of compounds, acyclic imides, is described. First, the N-metalation of selected secondary am des was examined, using various bases and solvents. The most efficient metalating agent was found to be butyllithium in tetrahydrofuran. The N-lithiated amides were then acylated at -60 °C, with an acid chloride or anhydride to afford the corresponding acyclic imide in high yields. A total of 14 acyclic imides were prepared in this manner, most of them being new compounds. Among the two workup procedures examined, aqueous and nonaqueous, the latter was found to be more efficient. Compared to the literature procedures, this novel method appears to be superior in yields, purity and the time required for the preparaton. In view of the fact that acyclic imides are considerably reactive, they may become useful intermediates in synthesis. T2 - Journal of the Serbian Chemical Society T1 - The preparation of N-alkyl acyclic imides VL - 61 IS - 2 SP - 69 EP - 76 UR - https://hdl.handle.net/21.15107/rcub_cherry_54 ER -
@article{ author = "Mićović, I.V. and Ivanović, Milovan and Lečić, V.M. and Roglić, Goran and Kiricojević, V.D. and Popović, J.B.", year = "1996", abstract = "An optimized method for the preparation of a little known class of compounds, acyclic imides, is described. First, the N-metalation of selected secondary am des was examined, using various bases and solvents. The most efficient metalating agent was found to be butyllithium in tetrahydrofuran. The N-lithiated amides were then acylated at -60 °C, with an acid chloride or anhydride to afford the corresponding acyclic imide in high yields. A total of 14 acyclic imides were prepared in this manner, most of them being new compounds. Among the two workup procedures examined, aqueous and nonaqueous, the latter was found to be more efficient. Compared to the literature procedures, this novel method appears to be superior in yields, purity and the time required for the preparaton. In view of the fact that acyclic imides are considerably reactive, they may become useful intermediates in synthesis.", journal = "Journal of the Serbian Chemical Society", title = "The preparation of N-alkyl acyclic imides", volume = "61", number = "2", pages = "69-76", url = "https://hdl.handle.net/21.15107/rcub_cherry_54" }
Mićović, I.V., Ivanović, M., Lečić, V.M., Roglić, G., Kiricojević, V.D.,& Popović, J.B.. (1996). The preparation of N-alkyl acyclic imides. in Journal of the Serbian Chemical Society, 61(2), 69-76. https://hdl.handle.net/21.15107/rcub_cherry_54
Mićović I, Ivanović M, Lečić V, Roglić G, Kiricojević V, Popović J. The preparation of N-alkyl acyclic imides. in Journal of the Serbian Chemical Society. 1996;61(2):69-76. https://hdl.handle.net/21.15107/rcub_cherry_54 .
Mićović, I.V., Ivanović, Milovan, Lečić, V.M., Roglić, Goran, Kiricojević, V.D., Popović, J.B., "The preparation of N-alkyl acyclic imides" in Journal of the Serbian Chemical Society, 61, no. 2 (1996):69-76, https://hdl.handle.net/21.15107/rcub_cherry_54 .