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

• Main Authors: Gui-Feng Kang, Gang Zhang
• Format: Article
• Language: English
• Published: Beilstein-Institut 2020-06-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: aldehydes; multicomponent reactions; nitrogen heterocycles; thiourea; triazinethiones
• Online Access: https://doi.org/10.3762/bjoc.16.120

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.