作为医药中间体，用于相关药物合成。
医药
合成路线 1（1. 合成：4295-99-2）
产率：100%
合成条件：at 110 - 120℃; for 1.50 h; Heating / reflux
实验步骤：实施例10-38（4-氰基四氢吡喃的合成）除了改变催化剂，溶剂和/或反应时间外，以与实施例9相同的方式，按实施例9进行反应。结果示于表1中。1。
参考文献：
- [1] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [2] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [3] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [4] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [5] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [6] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [7] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [8] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [9] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [10] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [11] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [12] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [13] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [14] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [15] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13 [16] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [17] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [18] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13 [19] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [20] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [21] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [22] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [23] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [24] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13 [25] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [26] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13 [27] Patent: JP5673729, 2015, B2. Location in patent: Paragraph 0068 [28] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [29] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [30] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [31] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 13-14 [32] Journal of the Chemical Society, 1930, p. 2525,2529 [33] Patent: EP1671937, 2006, A1. Location in patent: Page/Page column 15-16 [34] Patent: WO2018/29711, 2018, A2. Location in patent: Page/Page column 30
合成路线 2（2. 合成：4295-99-2）
产率：87%
合成条件：With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In tetrahydrofuran; ethyl acetate at 20℃; Inert atmosphere
实验步骤：向醛肟（0.01mol）的THF（10mL）溶液中加入T3P（15mol％，50％溶于EtOAc的溶液），并将所得反应混合物在室温下在氮气氛下搅拌1-2小时。 当通过TLC证实反应完成时，在真空下除去溶剂并将残余物用水（20mL）稀释。 产物用乙酸乙酯（2×20mL）萃取，合并的有机相用饱和NaHCO 3溶液（1×10mL）和盐水洗涤。 有机相用无水Na 2 SO 4干燥。 减压除去溶剂，得到所需的纯度良好的腈。
参考文献：
- [1] Tetrahedron Letters, 2011, vol. 52, # 10, p. 1074 - 1077
合成路线 3（3. 合成：4295-99-2）
产率：94%
合成条件：for 4 h; Reflux; Inert atmosphere
实验步骤：将亚硫酰氯（10.0mL，137mmol）加入到氧杂-4-甲酰胺（3.0g，23mmol）中，并将反应混合物回流4小时，然后将反应混合物倒在冰上并用NaOH（50％）碱化至pH 14。）。 将水溶液用EtOAc（3×50mL）萃取，干燥（Na 2 SO 4）并真空浓缩，得到产物，为浅黄色油状物（2.4g，94％）。 得到的产物不需要进一步纯化.IRνmax2961,2932,2851,2240,1468,1446,1390,1242,1125,1066,1011cm-1; 1H-NMR（CDCl3,500MHz）：3.91（2H， ddd，J 11.9,6.3,3.6,2×2-HA），3.61（2H，ddd，J 11.9,7.8,3.3,2×2-HB），2.91-2.85（1H，m，4-H），1.99 -1.92（2H，m，2×3-HA），1.91-1.84（2H，m，2×3-HB）; 13C-NMR（CDCl3,75MHz）：121.2,65.6,28.9,25.3; HRMS（ESI + ）：计算值C 6 H 10 NO（[M + H] +）：112.0756。 实测值：112.0754，Δ-1.8ppm。
参考文献：
- [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 11, p. 2629 - 2635 [2] Patent: US2007/111984, 2007, A1. Location in patent: Page/Page column 45 [3] Journal of the American Chemical Society, 1943, vol. 65, p. 370 [4] Patent: US2009/253679, 2009, A1. Location in patent: Page/Page column 54-55
