An asymmetric aza-Friedel-Crafts alkylation reaction between indoles and indolenines that were derived in situ from 3-indolinone-2-carboxylates has been developed by using 3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate as a catalyst. The reaction proceeded under mild conditions and provided chiral indol-3-yl-3-indolinone-2-carboxylate derivatives in good yields with excellent ee values (up to 98.6 %). Similarly, the Mannich-type addition of indoline-3-ones to indolenines provided heterodimers with vicinal chiral quaternary centers. This method was successfully applied to the construction of the core structure of trigonoliimine C.
A novel and efficient approach has been developed for the synthesis of a diverse range of hydroxyisoindolo[1,2‐b]benzothiadiazinedioxide derivatives through a sequential palladium catalyzed cross‐dehydrogenative coupling (CDC) and intramolecular cyclization. This method works not only with aryl aldehydes and alcohols but also with toluene to generate angularly fused heterocycles in good to excellent yields.
A strategy has been developed for the synthesis of dispiro‐3H‐indoles by employing a 3‐({[2‐(1H‐indol‐3‐yl)ethyl]amino}methyl)but‐3‐en‐1‐ol derivative and various aldehydes in a sequential Prins/Friedel–Crafts cyclization in the presence of readily accessible trifluoroacetic acid (TFA) under mild conditions over a short period of time. This method proceeded smoothly with a wide range of aldehydes and provided the products in good yields with a broad pattern of substituents.
Rh(III) catalyzed oxidative annulation of 2-aryl-1Hbenzo[d]imidazoles with 1,4-quinones has been achieved for the synthesis of a novel class of benzo[4,5]imidazo[1,2f]phenanthridine-1,4-dione frameworks through a sequential CÀ C and CÀ N bond formations in a single-step operation. This is the first report on the oxidative annulation of 2-aryl-1Hbenzo[d]imidazoles with 1,4-quinones to produce highly functionalized phenanthridine-1,4-dione derivatives.
A variety of novel thiazolidine derivatives (2-thioxothiazolidin-4-one and thiazolidine-2, 4-dione derivatives) have been prepared by using 2,4-diphenyl-2Hchromene-3-carbaldehyde and its derivatives as starting materials. This is the first example of the preparation of thiazolidine derivatives through this novel method. Structure evolution of the resulting thiazolidine derivatives leads to anticancer agents. Our preliminary data for some model compounds on three cancer cell lines (MCF7, A549 and B-16) suggested reasonable anticancer activity against the A549 and B-16 cell lines, with IC 50 values of 20.7 and 20.4 µM, respectively. This method is operationally simple and works with a diverse range of substrates.
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