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Novel Sultone Based Brønsted Acidic Ionic Liquids with Perchlorate Counter-Anion for One-pot Synthesis of 2H‑indazolo[2,1‑b]phthalazine‑triones
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2021-04-01 , DOI: 10.1016/j.molstruc.2020.129599 Fatemeh Arian , Mosadegh Keshavarz , Haleh Sanaeishoar , Neda Hasanzadeh
Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2021-04-01 , DOI: 10.1016/j.molstruc.2020.129599 Fatemeh Arian , Mosadegh Keshavarz , Haleh Sanaeishoar , Neda Hasanzadeh
Abstract Three novel sultone based Bronsted acidic ionic liquids are introduced. These ionic liquids were prepared in three similar two-steps reactions. The ring opening of 1,4-butane sultone was performed using 1,4-dimethyl piperazine or 1,10-phenantroline as nitrogen nucleophile sources to obtain zwitterions and then followed by acidification by treatment with perchloric acid to give the introduced ionic liquids. FTIR, 1HNMR, 13C-NMR, TGA and CHNS analysis techniques were used for the characterization of these ionic liquids. These ionic liquids are completely water soluble and have good thermal stability. Their catalytic efficiency was checked for the preparation of polycyclic 2H‑indazolo[2,1‑b]phthalazine‑trione compounds. Small amount (3-7 mmol%) of the prepared acidic ionic liquid catalysts is required and targeted products are obtained in short times (6-25 min) at high yields (86-96%). Moreover, the introduced acidic ionic liquids are completely green, environmental benign and task specific and simply recoverable up to six consecutive runs without significant decrease in their catalytic.
中文翻译:
具有高氯酸盐反阴离子的新型磺内酯基布朗斯台德酸性离子液体用于一锅法合成 2H-吲唑并[2,1-b]酞嗪三酮
摘要 介绍了三种新型磺内酯基布朗斯台德酸性离子液体。这些离子液体是在三个类似的两步反应中制备的。使用1,4-二甲基哌嗪或1,10-菲咯啉作为氮亲核试剂源进行1,4-丁烷磺内酯的开环以获得两性离子,然后用高氯酸处理酸化以得到引入的离子液体。FTIR、1HNMR、13C-NMR、TGA和CHNS分析技术用于表征这些离子液体。这些离子液体完全溶于水并具有良好的热稳定性。在制备多环 2H-吲唑并[2,1-b] 酞嗪三酮化合物时检查了它们的催化效率。需要少量(3-7 mmol%)制备的酸性离子液体催化剂,并在短时间内(6-25分钟)以高产率(86-96%)获得目标产物。此外,引入的酸性离子液体是完全绿色、无害环境和任务特定的,并且可以简单地回收多达六次连续运行,而不会显着降低其催化性能。
更新日期:2021-04-01
中文翻译:
具有高氯酸盐反阴离子的新型磺内酯基布朗斯台德酸性离子液体用于一锅法合成 2H-吲唑并[2,1-b]酞嗪三酮
摘要 介绍了三种新型磺内酯基布朗斯台德酸性离子液体。这些离子液体是在三个类似的两步反应中制备的。使用1,4-二甲基哌嗪或1,10-菲咯啉作为氮亲核试剂源进行1,4-丁烷磺内酯的开环以获得两性离子,然后用高氯酸处理酸化以得到引入的离子液体。FTIR、1HNMR、13C-NMR、TGA和CHNS分析技术用于表征这些离子液体。这些离子液体完全溶于水并具有良好的热稳定性。在制备多环 2H-吲唑并[2,1-b] 酞嗪三酮化合物时检查了它们的催化效率。需要少量(3-7 mmol%)制备的酸性离子液体催化剂,并在短时间内(6-25分钟)以高产率(86-96%)获得目标产物。此外,引入的酸性离子液体是完全绿色、无害环境和任务特定的,并且可以简单地回收多达六次连续运行,而不会显着降低其催化性能。