Synthesis of 4-Arylselanyl-1H-1,2,3-triazoles from Selenium-Containing Carbinols

Abstract

In this work, we present a simple way to achieve 4-arylselanyl-1H-1,2,3-triazoles from selenium-containing carbinols in a one-pot strategy. The selenium-containing carbinols were used as starting materials to produce a range of selanyl-triazoles in moderate to good yields, including a quinoline and Zidovudine derivatives. One-pot protocols are crucial to the current concerns about waste production and solvent consumption, avoiding the isolation and purification steps of the reactive terminal selanylalkynes. We could also isolate an interesting and unprecedented by-product with one alkynylselenium moiety connected to the triazole.

One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

“…Recently, Begini et al developed 4-arylselanyl-1 H -1,2,3-triazoles from the one-pot Cu-catalyzed (Cu(OAc) 2 ) reaction of selanylalkynylcarbinols and aryl azides in the presence of sodium ascorbate (10 mol%) in H 2 O and THF (1:1) mixed solvent at 50 °C ( Scheme 6 ) [ 56 ].…”

Organocatalytic Synthesis and DNA Interactive Studies of New 1,2,3‐triazolyl‐thiazolidines Hybrids

“…[26][27][28] In recent years, our research group has focused on the synthesis of novel molecules containing the 1,2,3-triazole unit and assessing their biological properties to explore new avenues for their utilization. [29][30][31][32][33][34] According to the literature, in addition to the broad pharmacological applications of thiazolidines, combining them with other classes of molecules with established properties leads to the creation of intriguing hybrid derivatives. Examples include thiazole-thiazolidinedione hybrids, [35] spirothiazolidines, [36] and thiazolidinone Cu(II) and Fe(III) complexes designed to investigate interactions with DNA and serum albumins.…”

“…In parallel with the interest in thiazolidines, the study of 1,2,3‐triazoles has also gained prominence for similar reasons: their diverse applications, both in pharmacology [23–25] and materials science [26–28] . In recent years, our research group has focused on the synthesis of novel molecules containing the 1,2,3‐triazole unit and assessing their biological properties to explore new avenues for their utilization [29–34] …”

Copper-catalyzed deacetonative Sonogashira coupling

“…Tertiary propargyl alcohols capable of undergoing a base-mediated C–C bond cleavage (the retro-Favorskii reaction 33 ) are easy to store and inexpensive precursors of terminal alkynes. 34 Several groups evaluated these substrates in the tandem deacetonative Sonogashira coupling under Pd catalysis (Scheme 1C). 35 In 2012, Tsai et al elaborated an aqueous Fe-catalyzed protocol requiring harsh reaction conditions (140 °C, 48 h) and stoichiometric amounts of Zn powder and applicable only to a limited number of aryl iodides.…”