Dataset Information

Tandem Protocol of Hexahydroquinoline Synthesis Using [H₂-DABCO][HSO₄]₂ Ionic Liquid as a Green Catalyst at Room Temperature.

ABSTRACT: Green, eco-benign, and sustainable synthesis is paramount in present chemistry. Here, a facile, efficient, and [H₂-DABCO][HSO₄]₂ ionic-liquid-catalyzed one-pot multicomponent synthesis of hexahydroquinolines was reported under ambient reaction conditions. The reaction of 1,3-dicarbonyls, malononitrile, and ammonium acetate with various aldehydes in the presence of an ionic liquid catalyst and EtOH solvent at room temperature afforded excellent yields (76-100%) of hexahydroquinolines under a short reaction time (5-15 min). Mild reaction conditions, broad substrate scope (28 derivatives), and column-chromatography-free synthesis with excellent catalytic efficiency and good recyclability rendered this protocol superior and practical. The greenness of the present method was assessed through eco-score and E-factor. The significant results in gram-scale synthetic conditions validate its applicability in industries as well as academia in the near future.

SUBMITTER: Sahiba N

PROVIDER: S-EPMC9933228 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature

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Publications

Tandem Protocol of Hexahydroquinoline Synthesis Using [H2-DABCO][HSO4]2 Ionic Liquid as a Green Catalyst at Room Temperature.

Sahiba Nusrat N Sethiya Ayushi A Teli Pankaj P Agarwal Shikha S

ACS omega 20230206 6

Green, eco-benign, and sustainable synthesis is paramount in present chemistry. Here, a facile, efficient, and [H2-DABCO][HSO4]2 ionic-liquid-catalyzed one-pot multicomponent synthesis of hexahydroquinolines was reported under ambient reaction conditions. The reaction of 1,3-dicarbonyls, malononitrile, and ammonium acetate with various aldehydes in the presence of an ionic liquid catalyst and EtOH solvent at room temperature afforded excellent yields (76-100%) of ...[more]

PMID: 36816668

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Project description:The role that interfaces play in the dynamics of liquids is a fundamental scientific problem with vast importance in technological applications. From material science to biology, e.g., batteries to cell membranes, liquid properties at interfaces are frequently determinant in the nature of chemical processes. For most liquids, like water, the influence of an interface falls off on a ∼1 nm distance scale. Room temperature ionic liquids (RTILs) are a vast class of unusual liquids composed of complex cations and anions that are liquid salts at room temperature. They are unusual liquids with properties that can be finely tuned by selecting the structure of the cation and anion. RTILs are being used or developed in applications such as batteries, CO2 capture, and liquids for biological processes. Here, it is demonstrated quantitatively that the influence of an interface on RTIL properties is profoundly different from that observed in other classes of liquids. The dynamics of planar thin films of the room temperature ionic liquid, 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide (BmimNTf2), were investigated using two-dimensional infrared spectroscopy (2D IR) with the CN stretch of SeCN- as the vibrational probe. The structural dynamics (spectral diffusion) of the thin films with controlled nanometer thicknesses were measured and compared to the dynamics of the bulk liquid. The samples were prepared by spin coating the RTIL, together with the vibrational probe, onto a surface functionalized with an ionic monolayer that mimics the structure of the BmimNTf2. Near-Brewster's angle reflection pump-probe geometry 2D IR facilitated the detection of the exceedingly small signals from the films, some of which were only 14 nm thick. Even in quarter micron (250 nm) thick films, the observed dynamics were much slower than those of the bulk liquid. Using a new theoretical description, the correlation length (exponential falloff of the influence of the interfaces) was found to be 28 ± 5 nm. This very long correlation length, ∼30 times greater than that of water, has major implications for the use of RTILs in devices and other applications.

Dataset Information

Tandem Protocol of Hexahydroquinoline Synthesis Using [H₂-DABCO][HSO₄]₂ Ionic Liquid as a Green Catalyst at Room Temperature.

Publications

Tandem Protocol of Hexahydroquinoline Synthesis Using [H<sub>2</sub>-DABCO][HSO<sub>4</sub>]<sub>2</sub> Ionic Liquid as a Green Catalyst at Room Temperature.

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