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A novel amphipathic low-melting complex salt: An efficient homogeneous catalyst for synthesis of pyran-annulated heterocyclic scaffolds and pyrido[2,3-d]pyrimidines
Journal of Molecular Liquids ( IF 5.3 ) Pub Date : 2020-03-25 , DOI: 10.1016/j.molliq.2020.112989
Maedeh Saeedi Mirak-Mahaleh , Kurosh Rad-Moghadam

The reaction of triethyl(sulfonyl) ammonium chlorosulfonate with 1,1,3,3-tetramethylguanidine (TMG) gave a low-melting complex salt with amphipathic and acidic characters. The salt has a great tendency towards solvation of organic substrates upon slight heating, so it was employed as a homogeneous acidic and functional ionic liquid catalyst in the expedient synthesis of 4H-benzo[b]pyrans, pyrano[3,2-c]quinolones, and pyrido[2,3-d]pyrimidines. The catalytic activity of the complex salt is much better than the simple salts composing it. Spectroscopic studies and chemical analysis of the salt revealed that its empirical formula is in agreement with neutralization of TMG by two H2SO4 molecules. The HSO4 anions of the salt seem to form extensive H-bonding with the constituting Cl and ammonium cations, resulting in melting point depression of the complex salt due to the melting points of pure triethylamine and TMG hydrochloride salts. Another significant feature of this solid salt is that it can preserve its composition even after several times of separation from aqueous extracts and can be handled easily without danger.



中文翻译:

一种新型的两亲性低熔点复合盐:一种合成吡喃环杂环骨架和吡啶并[2,3- d ]嘧啶的高效均相催化剂

三乙基(磺酰基)氯磺酸铵与1,1,3,3-四甲基胍(TMG)的反应生成了具有两亲性和酸性特征的低熔点复合盐。该盐在轻微加热下很容易溶解有机底物,因此在方便合成4 H-苯并[ b ]吡喃,吡喃并[3,2- c ]时被用作均相的酸性和功能性离子液体催化剂。喹诺酮和吡啶并[2,3- d ]嘧啶。复合盐的催化活性比组成它的简单盐要好得多。对该盐的光谱学研究和化学分析表明,该盐的经验公式与两种H 2 SO 4中和TMG一致。分子。所述HSO 4 -的盐的阴离子似乎以形成广泛氢键与构成氯-和铵阳离子,从而导致熔化配盐的点降低由于纯三乙胺和盐酸TMG盐的熔点。这种固体盐的另一个显着特征是,即使从水提取物中分离几次后,它也可以保持其组成,并且可以轻松操作而没有危险。

更新日期:2020-03-26
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