One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

Abstract

A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction.

Recent Advances on the s‐Triazine Scaffold with Emphasis on Synthesis, Structure‐Activity and Pharmacological Aspects: A Concise Review

“… [30] Kang et al . in 2020, described the synthesis of s ‐triazine‐2,4‐dithione analogue P25 in one‐pot manner through three‐component reactions [31] . A round bottom flask was charged with arylaldehyde, thiourea, and trimethyl orthoformate in DMF and was heated at 80 °C for 5 h, however, to achieve excellent yields of P25 , synthetic procedure employed 2.5 equiv.…”

A novel benzoylthiourea derivative with a triazinethione moiety: Synthesis and coordination with the organometallic fac-[Re(CO)3]+ core

“…The most common reported ring closure synthetic methodology leading to triazinethione analogs involved the reaction of a carboximidamide [28], or urea [29] with isothiocyanates. Recently, the 1,3,5triazine-2,4-dithione derivatives have been synthesized by a ring closure mechanism involving threecomponent reactions of arylaldehydes, thiourea, and orthoformates [30]. The sulfidation of triazine using phosphorus oxychloride and hydrogen sulfide has been also reported as a synthetic route to triazinethione derivatives [31].…”

Tri-armed Schiff base fluorescent sensor for the rapid recognition of Zn(ii): application in live cell imaging, test strips and TLC

“…The chemical and photophysical characteristics of these compounds can be effectively altered by modifying their cores and dendrons. 22,23 Also, the presence of nitrogen and oxygen coordination sites in the Schiff base can effectively bind with almost all the transition metal ions, causing a uorescence turn-on/turn-off response through the formation of a metal complex. 24,25 Schiff bases and their metal complexes possess antiinammatory, antitubercular, anticancer, antioxidative, and antifungal properties.…”

“…The chemical and photophysical characteristics of these compounds can be effectively altered by modifying their cores and dendrons. 22,23…”