微波促进合成2-酰氨基萘并噻唑类化合物

doi:10.6023/cjoc202410021

摘要/Abstract

发展了一种快速制备萘并[1,2-d]噻唑和萘并[2,1-d]噻唑的方法. 在微波辐射条件下, 以醋酸锰(III)为氧化剂, 3-(1-萘基)-1-取代酰基硫脲为原料, 高效制得2-取代酰氨基萘并[1,2-d]噻唑衍生物. 详细研究了氧化剂用量、溶剂、反应时间、反应温度及微波功率等因素对产率的影响. 实验结果表明, 2.5 equiv.的Mn(OAc)₃•2H₂O, 15 mL醋酸, 反应时间25 min, 反应温度100 ℃, 微波功率700 W为比较适宜的合成条件. 将该方法应用于2-取代酰氨基萘并[2,1-d]噻唑衍生物的合成时同样取得了令人满意的结果. 该合成方法具有操作简便、反应快速以及原子经济性好等优点.

关键词: 萘并噻唑, 微波, 醋酸锰, 硫脲

A simple and efficient approach for the synthesis of both naphtho[1,2-d]thiazole and naphtho[2,1-d]thiazole derivatives was developed. Under microwave irradiation, 2-substituented acylamino naphtho[1,2-d]thiazole derivatives were synthesized through the intramolecular cyclization reaction of 3-(1-naphthyl)-1-substituented acylthioureas promoted by manganese(III) acetate. The effects of factors such as amount of oxidant, solvent, reaction time, reaction temperature and microwave power on the yield were investigated. The results showed that 2.5 equiv. of Mn(OAc)₃•2H₂O, 15 mL of acetic acid, a reaction time of 25 min, a reaction temperature of 100 ℃ and a microwave power of 700 W were ralatively suitable synthesis conditions. When this method was applied to the synthesis of 2-substituted acylamino naphtho[2,1-d]thiazole derivatives, satisfactory results were also obtained. This method has the advantages of simple operation, rapid reaction and good atom economy.

Key words: naphthothiazole, microwave, manganese acetate, thiourea

引用此文

刘天宝, 苗豆豆, 彭艳芬, 章敏, 桂美芳, 毕威龙, 宗亚文. 微波促进合成2-酰氨基萘并噻唑类化合物[J]. 有机化学, 2025, 45(7): 2612-2619.

Tianbao Liu, Doudou Miao, Yanfen Peng, Min Zhang, Meifang Gui, Weilong Bi, Yawen Zong. Microwave-Assisted Synthesis of 2-Acylamino Naphthothiazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2612-2619.

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