Amirmahani Najmeh, Mahmoodi Nosrat O, Malakootian Mohammad, Pardakhty Abbas
Department of Chemistry, University Campus 2, University of Guilan, Rasht, Iran.
Environmental Health Engineering Research Center, Kerman University of Medical Sciences, Kerman, Iran.
MethodsX. 2020 Feb 20;7:100823. doi: 10.1016/j.mex.2020.100823. eCollection 2020.
In this study, a new and effective catalyst for the synthesis of pyridazino[1,2-]indazole, indazolo[2,1-]phthalazine and pyrazolo[1,2-]phthalazine derivatives was introduced. Triethanolammonium acetate ([TEAH][OAc]) accelerates the reaction in a one-pot and four-component condensation of aldehydes, hydrazine hydrate, succinic/phthalic anhydride, and 1,3-dicarbonyl compounds. The yield of the products is high, and the reaction conditions are mild and solvent-free. Furthermore, the model reaction was conducted in the presence of triethanolammonium sulphate ([TEAH][HSO] and triethanolammonium formate ([TEAH][HCOO]) under various conditions. In addition, the catalyst is recyclable, therefore, it can be reused several times. The structure of the obtained products was confirmed by comparing the M.P., IR, and H NMR. Advantages of this technique are as following:•Synthesis of novel, green, and one-pot and four-component condensation (4CC) under solvent-free conditions at room temperature.•The catalytic reaction is performed under mild and environmentally friendly conditions in short reaction times and excellent yields.•The catalyst is easily recycled and exhibits good chemical and structural stability.
在本研究中,引入了一种用于合成哒嗪并[1,2 - ]吲唑、吲唑并[2,1 - ]酞嗪和吡唑并[1,2 - ]酞嗪衍生物的新型高效催化剂。三乙醇铵醋酸盐([TEAH][OAc])在醛、水合肼、琥珀酸/邻苯二甲酸酐和1,3 - 二羰基化合物的一锅四组分缩合反应中加速反应。产物收率高,反应条件温和且无溶剂。此外,在各种条件下,以硫酸三乙醇铵([TEAH][HSO₄])和甲酸三乙醇铵([TEAH][HCOO])为模型进行反应。另外,该催化剂可回收利用,因此可重复使用多次。通过比较熔点、红外光谱和氢核磁共振谱确定了所得产物的结构。该技术的优点如下:
•在室温无溶剂条件下合成新型、绿色的一锅四组分缩合反应(4CC)。
•催化反应在温和且环保的条件下进行,反应时间短,产率优异。
•催化剂易于回收,具有良好的化学和结构稳定性。