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.
Highlights
The construction of nitrogen-containing heterocycles is one of the most prolific areas in organic chemistry that has drawn considerable attention from chemists due to their widespread occurrence in a variety of natural products [1,2,3,4], chemical materials [5,6], and medication [7]
In view of what was explained above, and as a result of our interest in developing novel multicomponent reactions to access diverse triazinethione derivatives, we recently synthesized a series of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)thiones from aldehydes, thiourea and suitable orthoformates
We explored the synthesis of 1,3,5-triazine-2,4-dithione derivatives by carrying out a set of experiments using benzaldehyde (1a, 1.0 equiv), thiourea (2, 1.0 equiv), and trimethyl orthoformate (3a, 1.0 equiv) as the model reaction (Table 1)
Summary
The construction of nitrogen-containing heterocycles is one of the most prolific areas in organic chemistry that has drawn considerable attention from chemists due to their widespread occurrence in a variety of natural products [1,2,3,4], chemical materials [5,6], and medication [7]. The resulting substituted thioureas underwent a cyclization reaction providing the desired triazinethiones (Scheme 1a and 1b). Multicomponent reactions (MCRs) gained much interest among synthetic organic chemists as well as in combinatorial chemistry and drug discovery as versatile tools for the construction of different biologically active compounds by combining three or Scheme 1: Strategies for the synthesis of triazinethiones.
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