Facile synthesis of 3-aryl-1-((4-aryl-1,2,3-selenadiazol-5-yl)sulfanyl)isoquinolines

Abstract

A new series of 1,2,3-selenadiazoles containing an aryl or a 3-arylisoquinoline sulfanyl moiety at carbons 4 and 5, respectively, was prepared by cyclization of the respective semicarbazones in the presence of selenium(II) oxide and tetrahydrofuran at 70–75°C. Semicarbazones required for the reaction were obtained from 2-((3-arylisoquinolin-1-yl)sulfanyl)-1-phenylethanones, I, by a reaction with semicarbazide hydrochloride in ethanol/water mixture and potassium acetate base.

Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents

“…More recently, ethoxycarbonyl hydrazones and tosylhydrazones were also used for the reaction with SeO 2 in acetic acid. A number of works on the synthesis and use of 1,2,3-selenadiazoles has been discussed in reviews [9,90,91,92] and in more recently published original papers [93,94,95,96,97,98,99,100]. Synthesis of novel benzopyrano-1,2,3-selenadiazole and spiro[benzopyrano]-1,3,4-thiadiazoline derivatives as possible antitumor agents is an example [96].…”

Green chemical approach: microwave assisted, titanium dioxide nanoparticles catalyzed, convenient and efficient C–C bond formation in the synthesis of highly functionalized quinolines and quinolinones

“…Further, the methods have shown tremendous advantages including simple reaction and easy work up procedure, rapid conversion, ambient reaction condition, ecofriendly, improved yields in comparison to conventional methods. 83 With our enormous interest in quinoline chemistry and environmentally benign synthesis, [84][85][86][87][88][89][90][91][92][93][94][95][96][97] in the present study the titanium dioxide nanoparticles, TiO 2 NPs has been explored as a solid support in the C-C bond formation for the synthesis of highly functionalized quinolines and quinolinones (Scheme 1). The methodology also included the solvent free microwave irradiation to afford the desired products in high purity and yield in a short time.…”

A convenient and efficient C–OH bond activation, PdCl2(PPh3)2catalyzed, C–C bond formation of tautomerizable quinolinones with the aid of BOP reagent and boronic acids

“…With our immense interest in the synthesis and diversication of heterocycles, especially in quinoline chemistry, [100][101][102][103][104][105][106][107][108][109][110][111][112][113] we were interested in applying the C-OH activation strategy with other types of cross-coupling reactions. Herein, we report our studies of the Suzuki-type reactions of the tautomerizable heterocycles activated by BOP reagent with various boronic acids (Scheme 1).…”