| 第 50 卷第 1 期 |  | Vol. 50 No. 1 | | 2020 年 2 月 | Feb 2020 |
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所屬欄目：醫藥及中間體
3-甲基-5-（2H-四唑-2-基）苯胺的合成研究 |
| 徐小娜1，柯 苗1，朱周靜2，劉 斌2
（1. 咸陽(yáng)職業(yè)技術(shù)學(xué)院 醫藥化工學(xué)院 陜西 咸陽(yáng) 712000；2. 陜西省中藥綠色制造技術(shù)協(xié)同創(chuàng )新中心，陜西國際商貿學(xué)院 醫藥學(xué)院 陜西 西安712046） |
| 摘 要：以3-甲基-5-硝基苯胺為原料，經(jīng)過(guò)重氮化、1，3-偶極環(huán)加成、硝基還原反應得到目標化合物3-甲基-5-（2H-四唑-2-基）苯胺（1），3步反應總收率31%。反應中間體及目標化合物結構經(jīng)1H NMR和ESI-MS表征�？疾炝酥氐磻挠绊懸蛩�，優(yōu)化反應條件為：n（3-甲基-5-硝基苯胺）∶n（亞硝酸鈉）= 1.0∶2.0，反應溫度0℃，反應時(shí)間30 min。優(yōu)化條件下，3-甲基-5-硝基苯-1-重氮四氟硼酸鹽（3）收率為87%。 |
| 關(guān)鍵詞：雜環(huán)化合物；四唑；苯胺；重氮化反應；1，3-偶極環(huán)加成反應 |
| 中圖分類(lèi)號：TQ246 文獻標識碼：A 文章編號：1009-9212（2020）01-0029-03 |
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| Synthesis of 3-Methyl-5-(2H-tetrazol-2-yl) aniline |
| XU Xiao-na1, KE Miao1, ZHU Zhou-jing2, LIU Bin2
(1. School of Pharmaceutical & Chemical Engineering, Xianyang Vocational Technical College, Xianyang 712000, China; 2. Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province, School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xi'an 712046, China) |
| Abstract：3-Methyl-5-(2H-tetrazol-2-yl) aniline was synthesized through a three-step reaction including diazo reaction, 1,3-dipolar cycloaddition and nitro-reduction using 3-methyl-5-nitroaniline as the starting material with an overall yield of 31%. The structure of the intermediate and product were characterized by 1H NMR and ESI-MS. The optimal conditions of diazo reaction were also investigated. The reaction conditions as follows: the dosage of NaNO2 is n(2)∶n(NaNO2)=1.0∶2.0; reaction temperature of 25℃; reaction time of 30 min. Compound 3 was obtained with a yield of 87% under this optimal reaction conditions. |
| Key words：heterocyclic compound; tetrazole; aniline; diazo reaction; 1,3-dipolar cycloaddition |
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基金項目：陜西省教育廳2020年度專(zhuān)項科研計劃項目（20JK0954）。
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作者簡(jiǎn)介：徐小娜（1985-），女，山東泰安人，講師，研究方向：天然產(chǎn)物及藥物合成研究（E-mail：xuxiaona@163.com）。
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收稿日期：2020-02-12
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