Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N‐arylacrylamides with Diorganyl Diselenides

Abstract

The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction of C−Se bond. A series of seleno oxindoles with pharmacological activity were obtained by using this well‐designed tandem cyclization strategy. The in vitro antitumor activity of the compounds was also screened through MTT assay. Results showed that the seleno oxindoles exhibited better antitumor activity than other oxindole derivatives.

Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity

“…The synthesis of the ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H- [1,2,4]triazolo [3,4-b][1,3,4]thiadiazine derivatives was performed using a two-step, one pot procedure. In order to optimize the chemistry, a model reaction was carried out using 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole 1, acetylacetone 2, 2,3-dimethoxybenzaldehyde 3 and 4-methoxyphenacylbromide 4 as starting materials (Scheme 1).…”

“…The synthesis of a new series of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H- [1,2,4]triazolo [3,4- 3,4]thiadiazine derivatives was carried out in an excellent yields via a onepot, four-component method using readily available starting materials. The reactions proceeds in such a way with high atom economy, leading to the formation of one C=N, two C-N, one C-C, and one C-S bonds in a single operation, giving multi-annulated products.…”

“…Heterocyclic structures are well-known components of various biologically active compounds. Nitrogen-containing hetero aromatics [1][2][3][4][5][6][7], such as triazole and pyrazole are well known to impart biological activity. Examples of marketed drugs based on a 1,2,4-triazole scaffold include voriconazole (an antifungal drug), forasartan (used for the treatment of hypertension), sitagliptin (an antidiabetic drug) and letrozole (a non-steroidal aromatase inhibitor for the treatment of breast cancer) (Fig.…”

“…We recently reported the synthesis of [1,2,4]triazolo [3,4b] [1,3,4]thiadiazines through the multi-component reaction (MCR) process [45]. The presence of a hydrazino group in these molecules offers the possibility to convert them into pyrazole moieties.…”

Electrochemically Enabled Selenium Catalytic Synthesis of 2,1-Benzoxazoles from o-Nitrophenylacetylenes

“…In addition, the controllability of the current and potential indicates that the oxidation or reduction ability of the reaction system is operable. Therefore, electrochemically enabled organocatalysis is a promising metal- and oxidant-free catalytic method . At the anode, the oxidation of organic catalysts could give intermediates with oxidizing properties.…”