Guo Wei, Liu Gongping, Deng Ling, Mei Weijie, Zou Xiaoying, Zhong Yumei, Zhuo Xiaoya, Fan Xiaolin, Zheng Lvyin
Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, China.
J Org Chem. 2021 Dec 17;86(24):17986-18003. doi: 10.1021/acs.joc.1c02313. Epub 2021 Nov 26.
A metal- and oxidant-free three-component desulfurization and deamination condensation of amidines, isothiocyanates, and hydrazines for the synthesis of structurally diverse fully substituted 1-1,2,4-triazol-3-amines is described. The reaction proceeds without the requirement of any external catalysts, metals, ligands, or oxidants. This [2 + 1 + 2] cyclization strategy involves C-N and C-S bond cleavage and the formation of new C-N bonds in one pot. This transformation provides a series of full substituted 1-1,2,4-triazol-3-amines with advantages of a broad substrates scope, mild reaction conditions, environmental friendliness, and easy gram-scale applications. The fluorescence and aggregation-induced emission (AIE) properties of selected products were further tested. These synthesized 1-1,2,4-triazol-3-amines may be worth investigating for further applications in the fields of organic chemistry, medicinal chemistry, and optical materials.
本文描述了一种用于合成结构多样的全取代1,2,4-三唑-3-胺的脒、异硫氰酸酯和肼的无金属和氧化剂的三组分脱硫脱氨基缩合反应。该反应无需任何外部催化剂、金属、配体或氧化剂即可进行。这种[2 + 1 + 2]环化策略涉及C-N和C-S键的断裂以及在一锅反应中形成新的C-N键。这种转化提供了一系列全取代的1,2,4-三唑-3-胺，具有底物范围广、反应条件温和、环境友好以及易于克级规模应用等优点。进一步测试了所选产物的荧光和聚集诱导发光（AIE）性质。这些合成的1,2,4-三唑-3-胺在有机化学、药物化学和光学材料领域的进一步应用可能值得研究。
