A Facile Synthetic Approach to 3-Halo-4-substituted-1,5-dihydro-4H-1,2,4-triazoline-5-thiones Based on Retro-Michael Addition

作者：Tian He; Liu Yuqiang; Li Xingwei; Xie Yafei; Liu Changying; Wang Jianwu^*; Zhao Guilong^*

来源：Chemical Research in Chinese Universities, 2017, 33(4): 587-593.

DOI：10.1007/s40242-017-6491-5

• Synthetic approach
• Protecting group
• Triazole
• Halogenation
• Regioselectivity
• Retro-Michael addition

A facile 3-step synthetic approach to 3-halo-4-substituted-1,5-dihydro-4H-1,2,4-triazoline-5-thiones (1a-1k) from corresponding unhalogenated 8a-8i was developed based on the strategy of retro-Michael addition, with the key steps being regioselective S-alkylation of compounds 8a-8i with ethyl 3-iodopropionate(12c) and alkaline cleavage of the propionate protecting group via retro-Michael addition. The synthetic approach was characterized by simplicity of operation and wide substrate scope.

• 出版日期2017-8
• 单位天津药物研究院有限公司; 山东大学