Metal-Free One-Pot Four-Component Cascade Annulation in Ionic Liquids at Room Temperature: Convergent Access to Thiazoloquinolinone Derivatives,The Journal of Organic Chemistry

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Metal-Free One-Pot Four-Component Cascade Annulation in Ionic Liquids at Room Temperature: Convergent Access to Thiazoloquinolinone Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-07-06 00:00:00 , DOI: 10.1021/acs.joc.8b00814
Anshu Singh ₁ , Abhijeet Srivastava ₁ , Maya Shankar Singh ₁

Affiliation

An efficient, eco-friendly, and highly convergent one-pot route to privileged thiazoloquinolinone derivatives has been developed via four-component cascade coupling (4CCC) of α-enolic dithioesters, cysteamine/2-aminothiophenols, aldehydes, and cyclic 1,3-diketones in recyclable [EMIM][EtSO₄] ionic liquid at room temperature for the first time. The reaction proceeds via a N,S-acetal formation, Knoevenagel condensation, aza-ene reaction, imine–enamine/keto–enol tautomerization, and intramolecular N-cyclization cascade sequence. The merit of the protocol is highlighted by its efficacy of forming consecutive five new bonds (two C–C, two C–N, and one C–S) and two rings with all reactants being efficiently utilized. The operational simplicity, sustainability, mild conditions, excellent yields, tolerance of wide functional groups, and avoidance of expensive/toxic reagents are additional attributes to this domino four-component protocol. Notably, the products were easily separated from the ionic liquid, and thus the ionic liquid obtained was reused four times without considerable loss of any activity.

中文翻译：

室温下离子液体中的无金属一锅四组分级联环流：噻唑并喹啉酮衍生物的聚合进出

通过α-烯醇二硫代酸酯，半胱胺/ 2-氨基硫代酚，醛和环状1,3-的四组分级联反应（4CCC），开发了一种高效，生态友好且高度收敛的一锅合成特权噻唑基喹啉酮衍生物的途径。室温下可循环使用的[EMIM] [EtSO ₄ ]离子液体中的二酮首次出现。反应通过N，S进行-缩醛形成，Knoevenagel缩合，氮杂-烯反应，亚胺-烯胺/酮-烯醇互变异构和分子内N-环化级联序列。该协议的优点突出在于它可以形成连续的五个新键（两个C–C，两个C–N和一个C–S）和两个环，并有效利用所有反应物的功效。操作简便，可持续性，温和条件，优异的收率，宽泛的官能团耐受性以及避免使用昂贵/有毒的试剂是该多米诺骨牌四组分方案的其他属性。值得注意的是，产物易于与离子液体分离，因此获得的离子液体被重复使用四次而没有任何活性的显着损失。

更新日期：2018-07-06

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