Sedative–hypnotic profile of novel isatin ketals

Green synthesis of novel isatin thioketal derivatives under solvent-free conditions

“…′ -indolin]-2 ′ -one and α,β-unsaturated esters were synthesized in our laboratory according to the literature procedures (10,14). Dihaloalkanes were purchased from Merck and used without further purification.…”

“…Isatin ketals have anxiolytic (7), psychotropic (8), and anticonvulsant activities (9). For instance, spiro [1,3-dioxolane-2,3 ′ -indol]-2 ′ (1 ′ H)-one (I) has sedative, hypnotic, and anesthetic properties (10).…”

Heck Reaction in Diols and Cascade Formation of Cyclic Ketals

“…Unlike Heck reactions of electron-deficient olefins such as acrylates, which generally give exclusively bsubstitution products, 10d,12 electron-rich olefins tend to give a mixture of products when allowed to react under the same conditions. 8f,10e,13 Two catalysts that exemplify this problem are the Hermann-Beller palladacycle 14 and Fu's Pd-P(t-Bu) 3 catalysts. 13h Both are successful catalysts for reactions of electron-deficient olefins, providing bproducts exclusively; yet when electron-rich olefins are employed a mixture of products are formed, with the b/a ratios becoming 13:10 and 1:4, for instance.…”

“…In fact, a wide range of aryl groups can be tolerated, including electron-deficient (entries [1][2][3]8), electron rich (entries 9-13), and sterically demanding (entries 4,12). Heterocyclic aryl bromides also reacted to yield the cyclic ketals in good yields (entries 14,15).…”

“…1,2 Most interestingly, a number of biologically active molecules are known to contain the cyclic ketal moiety. 3 Figure 1 shows a few selected examples. Ketoconazole and propiconazole are both antifungal agents, the former being used in many medical applications, while the latter being a widely used agricultural fungicide.…”