Synthesis of N-heterocyclic compounds using ,-dimethylacetamides as an electrophilic carbon source.

In this study, N-heterocyclic compounds were synthesized using nitrogen-containing nucleophilic substrates and electrophilic carbon sources derived from ,-dimethylacetamide (DMAc). Depending on the nucleophilic groups, N-heterocyclic compounds such as 4-quinazolinones, pyrrole-quinoxalines, and dihydro-benzothiadiazine dioxides were produced. Carbon, adjacent to the nitrogen in DMAc, was activated in the presence of FeCl·6HO and di--butyl peroxide (DTBP).

Evo312: An Evodiamine Analog and Novel PKCβI Inhibitor with Potent Antitumor Activity in Gemcitabine-Resistant Pancreatic Cancer.

As an obstinate cancer pancreatic cancer (PC) poses a major challenge due to limited treatment options which include resection surgery, radiation therapy, and gemcitabine-based chemotherapy. In cancer cells, protein kinase C βI (PKCβI) participates in diverse cellular processes, including cell proliferation, invasion, and apoptotic pathways. In the present study, we created a scaffold to develop PKCβI inhibitors using evodiamine-based synthetic molecules.

Iron-Catalyzed Oxidative Cyclization of 2-Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines.

Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di--butyl peroxide. Then, the quinoline scaffold is synthesized through imine condensation/radical cyclization/oxidative aromatization.

Chemoselective α-Alkylation and α-Olefination of Arylacetonitriles with Alcohols Iron-Catalyzed Borrowing Hydrogen and Dehydrogenative Coupling.

α-Alkyl and α-olefin nitriles are very important for organic synthesis and medicinal chemistry. However, different types of catalysts are employed to achieve either α-alkylation of nitriles by borrowing hydrogen or α-olefination by dehydrogenative coupling methods. Designing and developing high-performance earth-abundant catalysts that can procure different products from the same starting materials remain a great challenge.

Iron-catalyzed one-pot synthesis of quinoxalines: transfer hydrogenative condensation of 2-nitroanilines with vicinal diols.

Here, we report iron-catalyzed one-pot synthesis of quinoxalines transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (η4-cyclopentadienone) iron complex, which is well known as the Knölker complex, catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding carbonyl and 1,2-diaminobenzene intermediates were generated . Trimethylamine N-oxide was used to activate the iron complex.

Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene.

Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di--butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde . Oxygen played a crucial role in the oxidation process to accelerate benzaldehyde formation.

First Total Synthesis of Gaylussacin and Its Stilbene Derivatives.

Gaylussacin (), a stilbene glucoside, has been isolated from and is used in Korean folk medicine. Although it was first isolated in 1972, the synthesis of gaylussacin has never been reported. Herein, we report the first total synthesis of gaylussacin in six steps with an overall yield of 23.

Iron(0)-Catalyzed Transfer Hydrogenative Condensation of Nitroarenes with Alcohols: A Straightforward Approach to Benzoxazoles, Benzothiazoles, and Benzimidazoles.

The iron-catalyzed hydrogen transfer strategy has been applied to the redox condensation of -hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism.

Direct Synthesis of Pyrrolo[1,2-α]quinoxalines Iron-Catalyzed Transfer Hydrogenation between 1-(2-Nitrophenyl)pyrroles and Alcohols.

Herein, we describe novel iron-catalyzed transfer hydrogenation between alcohols and 1-(2-nitrophenyl)pyrroles for the synthesis of pyrrolo[1,2-α]quinoxalines. The tricarbonyl (η-cyclopentadienone) iron complex catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding aldehydes and aniline were generated . The resulting Pictet-Spengler-type annulation/oxidation completed the quinoxaline structure formation.

One-Pot Synthesis of 4-Quinolone via Iron-Catalyzed Oxidative Coupling of Alcohol and Methyl Arene.

Herein, we describe the iron(III)-catalyzed oxidative coupling of alcohol/methyl arene with 2-amino phenyl ketone to synthesize 4-quinolone. Alcohols and methyl arenes are oxidized to the aldehyde in the presence of an iron catalyst and di--butyl peroxide, followed by a tandem process, condensation with amine/Mannich-type cyclization/oxidation, to complete the 4-quinolone ring. This method tolerates various kinds of functional groups and provides a direct approach to the synthesis of 4-quinolones from less functionalized substrates.

Iron-Catalyzed Acceptorless Dehydrogenative Coupling of Alcohols With Aromatic Diamines: Selective Synthesis of 1,2-Disubstituted Benzimidazoles.

Benzimidazoles are important -heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products.

Synthesis of 2-aryl quinazolinones via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds.

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95%.