5-(4-硝基苯基)-1H-四唑可用作有机合成中间体和医药中间体，主要用于实验室研发过程和医药化工生产过程中。
有机合成中间体; 医药中间体
路线1：以醛肟为原料
- 步骤: 将InCl₃（3 mol%）加入到含有醛肟（1 mmol）和NaN₃（1.5 mmol）的DMF（5 mL）搅拌溶液中，加热至120℃反应；反应完成后冷却至室温，依次加入H₂O、2M HCl水溶液和EtOAc，分离有机层，水层用EtOAc萃取，合并有机萃取液，洗涤、干燥、过滤、减压蒸发溶剂，硅胶柱色谱纯化（洗脱剂：EtOAc-己烷（9:1））。
- 条件: 120℃，21 h，TLC监测反应完成；
- 收率: 84%；
- 参考文献: [1] Synlett, 2016, vol. 27, #8, p.1241-1244；[2] Tetrahedron Letters, 2012, vol.53, #29, p.3706-3709；[3] Synthesis (Germany), 2018, vol.50, #6, p.1293-1300；[4] Synlett, 2016, vol.27, #15, p.2225-2228；[5] Tetrahedron Letters, 2016, vol.57, #5, p.523-524；[6] Inorganic Chemistry, 2017, vol.56, #12, p.6849-6863
路线2：以4-氯苄腈为原料
- 步骤: 将4-氯苄腈（2 mmol）、NaN₃（4 mmol）、Sc(OTf)₃（0.4 mmol）和异丙醇-水（3:1，8 mL）加入微波容器，微波辐射160℃反应1 h；反应后冷却，用饱和碳酸氢钠水溶液稀释，乙酸乙酯洗涤，酸化后乙酸乙酯萃取，合并有机层干燥、浓缩、重结晶。
- 条件: 160℃，1 h，微波辐射，密封管；
- 收率: 100%；
- 参考文献: [1] Journal of the Brazilian Chemical Society, 2012, vol.23, #12, p.2197-2203；[2] Synthetic Communications, 2015, vol.45, #2, p.218-225；[3] Medicinal Chemistry, 2017, vol.13, #4, p.359-364；[4] Journal of Heterocyclic Chemistry, 2010, vol.47, #4, p.913-922；[5] Polyhedron, 2011, vol.30, #15, p.2606-2610；[6] RSC Advances, 2015, vol.5, #62, p.49849-49860；[7] RSC Advances, 2016, vol.6, #38, p.31850-31860；[8] RSC Advances, 2016, vol.6, #39, p.32653-32660；[9] Transition Metal Chemistry, 2017, vol.42, #2, p.131-136；[10] MedChemComm, 2017, vol.8, #10, p.1953-1964；[11] Monatshefte fur Chemie, 2013, vol.144, #9, p.1407-1410；[12] RSC Advances, 2015, vol.5, #84, p.68558-68564；[13] Applied Organometallic Chemistry, 2018, vol.32, #9；[14] Tetrahedron Letters, 2008, vol.49, #17, p.2824-2827；[15] Synthetic Communications, 2010, vol.40, #17, p.2624-2632；[16] Synthetic Communications, 2012, vol.42, #16, p.2375-2381；[17] Journal of Molecular Catalysis A: Chemical, 2014, vol.393, p.18-29；[18] Journal of Chemical Research, 2015, vol.39, #6, p.321-323；[19] RSC Advances, 2016, vol.6, #61, p.56638-56646；[20] Applied Organometallic Chemistry, 2017, vol.31, #7；[21] Synthetic Communications, 2018, vol.48, #2, p.175-187；[22] Research on Chemical Intermediates, 2018, vol.44, #2, p.1363-1380；[23] New Journal of Chemistry, 2018, vol.42, #16, p.13754-13762；[24] Journal of Organic Chemistry, 2004, vol.69, #8, p.2896-2898；[25] Journal of Organic Chemistry, 2000, vol.65, #23, p.7984-7989；[26] Journal of Organic Chemistry, 2011, vol.76, #21, p.9090-9095；[27] Chinese Chemical Letters, 2012, vol.23, #2, p.161-164；[28] Tetrahedron Letters, 2014, vol.55, #24, p.3507-3510；[29] Tetrahedron Letters, 2014, vol.55, #41, p.5683-5686；[30] Heterocycles, 2014, vol.89, #9, p.2137-2150；[31] Synthetic Communications, 2015, vol.45, #8, p.1023-1030；[32] Applied Organometallic Chemistry, 2015, vol.29, #11, p.730-735；[33] Catalysis Science and Technology, 2015, vol.5, #9, p.4452-4457；[34] Applied Organometallic Chemistry, 2016, vol.30, #11, p.897-904；[35] Organic Preparations and Procedures International, 2017, vol.49, #4, p.346-354；[36] Tetrahedron Letters, 2018, vol.59, #5, p.445-449；[37] Applied Organometallic Chemistry, 2018, vol.32, #8；[38] Journal of Organic Chemistry, 2010, vol.75, #19, p.6468-6476；[39] Tetrahedron Letters, 2013, vol.54, #49, p.6779-6781；[40] Transition Metal Chemistry, 2017, vol.42, #8, p.703-710；[41] Chemical Communications, 2010, vol.46, #3, p.448-450；[42] Angewandte Chemie - International Edition, 2011, vol.50, #15, p.3525-3528；[43] Patent: WO2012/24495, 2012, A1；[44] Journal of Sulfur Chemistry, 2018, vol.39, #3, p.237-251；[45] Journal of Organometallic Chemistry, 2018, vol.870, p.16-22；[46] Synthesis, 2009, #13, p.2175-2178；[47] Journal of Chemical Sciences, 2011, vol.123, #1, p.75-79；[48] Journal of Medicinal Chemistry, 2012, vol.55, #17, p.7392-7416；[49] Patent: WO2012/135641, 2012, A2；[50] Journal of Organometallic Chemistry, 2013, vol.738, p.41-48；[51] Journal of Organometallic Chemistry, 2013, vol.743, p.87-96；[52] Applied Organometallic Chemistry, 2017, vol.31, #12；[53] Applied Organometallic Chemistry, 2018, vol.32, #6；[54] Tetrahedron, 2007, vol.63, #2, p.492-496；[55] Synlett, 2010, #3, p.391-394；[56] RSC Advances, 2015, vol.5, #126, p.104087-104094；[57] Journal of Nanoscience and Nanotechnology, 2017, vol.17, #3, p.1992-1999；[58] Applied Organometallic Chemistry, 2017, vol.31, #9；[59] Synthetic Communications, 2011, vol.41, #20, p.3053-3059；[60] Mendeleev Communications, 2011, vol.21, #6, p.334-336；[61] RSC Advances, 2013, vol.3, #13, p.4362-4371；[62] Journal of Chemical Research, 2013, vol.37, #11, p.665-667；[63] RSC Advances, 2015, vol.5, #16, p.12372-12381；[64] Chemical Papers, 2015, vol.69, #9, p.1231-1236；[65] Applied Organometallic Chemistry, 2016, vol.30, #8, p.705-712；[66] RSC Advances, 2016, vol.6, #99, p.96623-96634；[67] Synlett, 2018, vol.29, #7, p.874-879；[68] Polyhedron, 2019, vol.157, p.374-380；[69] Journal of Chemical Research, 2017, vol.41, #1, p.25-29；[70] New Journal of Chemistry, 2014, vol.38, #7, p.3078-3083；[71] Tetrahedron Letters, 2016, vol.57, #51, p.5815-5819；[72] Applied Organometallic Chemistry, 2018, vol.32, #8；[73] Bulletin of the Korean Chemical Society, 2011, vol.32, #11, p.4001-4004；[74] Tetrahedron Letters, 2014, vol.55, #25, p.3557-3560；[75] Bioorganic Chemistry, 2018, vol.79, p.201-211；[76] Russian Journal of Organic Chemistry, 2007, vol.43, #5, p.765-767；[77] Synthetic Communications, 2017, vol.47, #7, p.695-703；[78] Chinese Chemical Letters, 2010, vol.21, #9, p.1029-1032；[79] Chinese Journal of Chemistry, 2011, vol.29, #1, p.131-134；[80] Tetrahedron Letters, 2013, vol.54, #1, p.106-109；[81] Journal of the Iranian Chemical Society, 2012, vol.9, #5, p.799-803；[82] Molecules, 2015, vol.20, #12, p.22757-22766；[83] New Journal of Chemistry, 2013, vol.37, #10, p.3261-3266；[84] Tetrahedron Letters, 2009, vol.50, #31, p.4435-4438；[85] Asian Journal of Chemistry, 2013, vol.25, #1, p.393-396；[86] Synthesis (Germany), 2014, vol.46, #6, p.781-786；[87] New Journal of Chemistry, 2015, vol.39, #6, p.4814-4820；[88] Journal of Chemical Sciences, 2016, vol.128, #1, p.93-99；[89] Bioorganic and Medicinal Chemistry, 2017, vol.25, #20, p.5278-5289；[90] Australian Journal of Chemistry, 2017, vol.70, #10, p.1127-1137；[91] Bulletin of the Korean Chemical Society, 2015, vol.36, #1, p.198-202；[92] Journal of the Iranian Chemical Society, 2018, vol.15, #4, p.831-838；[93] Chemistry Letters, 2012, vol.41, #8, p.814-816；[94] European Journal of Organic Chemistry, 2014, vol.2014, #2, p.436-441；[95] RSC Advances, 2014, vol.4, #69, p.36713-36720；[96] European Journal of Organic Chemistry, 2014, vol.2014, #2, p.436-441；[97] Heteroatom Chemistry, 2011, vol.22, #2, p.168-173；[98] Patent: EP946508, 2009, B1；[99] Polyhedron, 2015, vol.95, p.69-74；[100] Synthesis (Germany), 2018, vol.50, #17, p.3430-3435
路线3：以醛为原料
- 步骤: 将醛（1 mmol）、盐酸羟胺（2 mmol）和叠氮化钠（2 mmol）依次加入到(NH₄)₄Ce(SO₄)₄·2H₂O（20 mol%）的DMF（5 mL）溶液中，回流反应9 h；反应完成后用HCl（4N）处理，倒入水中用乙酸乙酯萃取，合并有机层干燥、浓缩，硅胶柱色谱纯化（洗脱剂：石油醚/乙酸乙酯（75:25））。
- 条件: 回流，9 h，TLC监测反应；
- 收率: 68%；
- 参考文献: [1] RSC Advances, 2016, vol.6, #94, p.91999-92006；[2] Applied Organometallic Chemistry, 2018, vol.32, #4；[3] Synlett, 2012, vol.23, #20, p.2927-2930；[4] New Journal of Chemistry, 2015, vol.39, #3, p.2116-2122；[5] Synthesis (Germany), 2013, vol.45, #4, p.507-510；[6] Tetrahedron Letters, 2018, vol.59, #14, p.1385-1389；[7] Synthetic Communications, 2011, vol.41, #14, p.2081-2085；[8] Bioorganic and Medicinal Chemistry, 2014, vol.22, #7, p.2220-2235；[9] Tetrahedron Letters, 2016, vol.57, #5, p.523-524；[10] Synthetic Communications, 2017, vol.47, #7, p.695-703
