医药拉帕替尼中间体；药物化学与有机合成中间体，是具有抗真菌活性化合物喹唑啉二硒化合物的合成中间体；结构中的氯原子可以被亲核试剂例如有机胺，醇类化合物进攻得到脱氯官能团化的产物；碘单元可以很容易地进行偶联反应和相应的取代反应进行应用转化。
医药;有机合成
路线1：Vilsmeier试剂法
- 步骤：在氮气下向搅拌的无水二甲基甲酰胺（DMF）（3.20ml）在1,2-二氯乙烷（DCE）（10ml）中的溶液中，在冰水浴中冷却，滴加草酰氯溶液（5.2ml，60毫摩尔，在DCE（25毫升）中）。添加结束后，除去冷浴，将反应混合物在室温下搅拌5分钟。在氮气流下分批加入6-碘-喹唑啉-4-醇（5.0g，18mmol），并将混合物立即加热至回流。继续加热4.5小时，然后冷却至室温。将反应混合物倒入过量的冰水混合物（约300ml）中并用DCM（约500ml）萃取。用DCM（2×50ml）进一步萃取水层。将合并的有机萃取液干燥（Na2SO4）并减压浓缩，得到所需产物。
- 条件：Vilsmeier试剂；1,2-二氯乙烷；回流4.5小时
- 收率：99%
- 参考文献：[1] Patent: US2005/101617, 2005, A1. Location in patent: Page/Page column 6 [2] Patent: WO2011/2523, 2011, A1. Location in patent: Page/Page column 43 [3] Patent: KR2017/15848, 2017, A. Location in patent: Paragraph 0067; 0071; 0072 [4] Patent: CN106317026, 2017, A. Location in patent: Paragraph 0075; 0076; 0077; 0078 [5] Patent: CN103772411, 2016, B. Location in patent: Paragraph 0017; 0027; 0028 [6] Patent: US2008/51422, 2008, A1. Location in patent: Page/Page column 13-14 [7] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5531 - 5538 [8] Patent: EP2744501, 2016, B1. Location in patent: Paragraph 0156; 0157 [9] Patent: EP2090575, 2009, A1. Location in patent: Page/Page column 61 [10] Organic Process Research and Development, 2005, vol. 9, # 4, p. 440 - 450 [11] Patent: US2006/281772, 2006, A1. Location in patent: Page/Page column 58-59 [12] Organic Process Research and Development, 2007, vol. 11, # 3, p. 406 - 413 [13] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 27 - 37 [14] Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1220 - 1227 [15] Patent: CN106986895, 2017, A. Location in patent: Paragraph 0012; 0113
路线2：草酰氯-DMF法
- 步骤：在氮气下向搅拌的无水二甲基甲酰胺（DMF）（3.20ml）在1,2-二氯乙烷（DCE）（10ml）中的溶液中，在冰水浴中冷却，滴加草酰氯溶液（5.2ml，60毫摩尔，在DCE（25毫升）中）。添加结束后，除去冷浴，将反应混合物在室温下搅拌5分钟。在氮气流下分批加入6-IODO-QUINAZOLIN-4-OL（5.0g，18mmol），并将混合物立即加热至回流。继续加热4.5小时，然后冷却至室温。将反应混合物倒入过量的冰水混合物（约300ml）中并用DCM（约500ml）萃取。用DCM（2×50ml）进一步萃取水层。将合并的有机萃取液干燥（Na2SO4）并减压浓缩，得到所需产物。
- 条件：草酰氯；N,N-二甲基甲酰胺；1,2-二氯乙烷；回流4.5小时
- 收率：99%
- 参考文献：[1] Patent: WO2004/46101, 2004, A2. Location in patent: Page 19-20 [2] Patent: CN105085496, 2018, B. Location in patent: Paragraph 0038; 0039 [3] Patent: CN103772371, 2016, B. Location in patent: Paragraph 0054; 0055 [4] Patent: WO2013/25958, 2013, A1. Location in patent: Page/Page column 55; 56 [5] Patent: WO2008/33747, 2008, A2. Location in patent: Page/Page column 169 [6] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790 [7] Patent: WO2008/67144, 2008, A2. Location in patent: Page/Page column 23 [8] Patent: WO2006/26313, 2006, A2. Location in patent: Page/Page column 23 [9] Patent: WO2006/113649, 2006, A1. Location in patent: Page/Page column 46 [10] Patent: US2011/281896, 2011, A1. Location in patent: Page/Page column 7 [11] Patent: WO2013/116786, 2013, A1. Location in patent: Page/Page column 18 [12] Patent: WO2014/134169, 2014, A1. Location in patent: Page/Page column 5 [13] Patent: WO2005/120512, 2005, A2. Location in patent: Page/Page column 23 [14] Patent: WO2005/120504, 2005, A2. Location in patent: Page/Page column 30 [15] Patent: WO2004/43940, 2004, A1. Location in patent: Page 82
路线3：三氯氧化磷-三乙胺法
- 步骤：在装有搅拌器，温度计和回流冷凝器的20mL体积的玻璃容器中放入2.00g（7.35mmol）的6-碘喹唑啉-4-酮，1.24g（8.09mmol）的三氯氧化磷和10mL甲苯在氮气氛中的含量。在室温下搅拌混合物的同时，依次加入0.82g（8.09mmol）三乙胺。将所得混合物加热至75℃，并使反应进行2小时。反应完成后，将反应混合物冷却至室温，加入100mL甲醇。将混合物在相同温度下搅拌15分钟，得到产物。
- 条件：三氯氧化磷；三乙胺；甲苯；75℃反应2小时
- 收率：99%
- 参考文献：[1] Patent: EP1481971, 2004, A1. Location in patent: Page 10 [2] Patent: EP1481971, 2004, A1. Location in patent: Page 11 [3] Patent: EP1481971, 2004, A1. Location in patent: Page 9-10 [4] Patent: EP1481971, 2004, A1. Location in patent: Page 11 [5] Patent: EP1481971, 2004, A1. Location in patent: Page 11 [6] Patent: EP1481971, 2004, A1. Location in patent: Page 11 [7] Patent: EP1481971, 2004, A1. Location in patent: Page 10-11 [8] Patent: EP1481971, 2004, A1. Location in patent: Page 11 [9] Patent: EP1481971, 2004, A1. Location in patent: Page 11 [10] Patent: WO2009/63054, 2009, A1. Location in patent: Page/Page column 69
