I₂/DMSO-catalyzed one-pot approach for the synthesis of 1,3,4-selenadiazoles

Abstract

A three-component cascade reaction for the synthesis of 1,3,4-selenadiazoles and their derivatives from arylaldehydes, hydrazine, and elemental selenium by using molecular iodine is reported.

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

“…1,8‐Dioxo‐decahydroacridine derivatives 170 were efficiently synthesized by the three‐component reaction of aromatic aldehydes, sulphanilamide and 5,5‐dimethyl‐1,3‐cyclohexanedione with iodine in propanol in high to excellent yields (Scheme 88). [163] …”

“…Synthesis of 1,8-dioxo-decahydroacridine derivatives, oxospirotricyclic furopyrimidines, polyazaheterocycles and 1,3,5-selenadiazoles from aromatic aldehydes 1,8-Dioxo-decahydroacridine derivatives 170 were efficiently synthesized by the three-component reaction of aromatic aldehydes, sulphanilamide and 5,5-dimethyl-1,3-cyclohexanedione with iodine in propanol in high to excellent yields (Scheme 88). [163] Bowroju and Bavanthula [164] reported the synthesis of selendiazoles 171via a three-component reaction of hydrazine, arylaldehydes and elemental selenium in presence of catalytic amount of molecular iodine (Scheme 88). The reaction proceeds via a radical pathway.…”

First Exclusive Stereo‐ and Regioselective Preparation of 5‐Arylimino‐1,3,4‐Selenadiazole Derivatives: Synthesis, NMR analysis, and Computational Studies

“…Because the preceding series of methods developed decades ago suffers from drawbacks that include instability and stench of selenium species used, purification challenges, harsh reaction conditions, low yields, and limited substrate scope, four recent improved synthetic approaches have been described [54–57] . In 2021, Wei et al .…”

“…The final product is formed by aromatization after a prototropic shift. Bowroju and Bavanthul reported an iodine/DMSO‐catalyzed one‐pot three‐component cascade reaction to make 1,3,4‐selenadiazoles from aromatic aldehydes, NH 2 NH 2 , and elemental selenium [56] . The reactions required refluxing for 4 h at 150 °C.…”

“…[53] Because the preceding series of methods developed decades ago suffers from drawbacks that include instability and stench of selenium species used, purification challenges, harsh reaction conditions, low yields, and limited substrate scope, four recent improved synthetic approaches have been described. [54][55][56][57] In 2021, Wei et al successfully demonstrated the use N-tosylhydrazones in the synthesis of 1,3,4-selenadiazol-2-amines using KSeCN as the Se source, N-thiocyanatosuccinimide (NCS), and scandium triflate (ScOTf) 3 . [54] Preparation of 2-amino-1,3,4-selenadiazoles was also possible through another reaction sequence from isoselenocyanates, hydrazine hydrate and aryl aldehydes that initially give substituted selenohydrazones through the intermediacy of selenosemicarbazides, followed by intramolecular cycloselenisation ensuing treatment of the selenohydrazone with NBS and NaOAc.…”