CN109053600A - 一种4-炔基喹唑啉类化合物的制备方法 - Google Patents
一种4-炔基喹唑啉类化合物的制备方法 Download PDFInfo
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
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- 150000001345 alkine derivatives Chemical class 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
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Abstract
本发明公开了属于有机合成技术领域的一种4‑炔基喹唑啉类化合物的制备方法。所述方法为：4‑炔基苯并噁嗪(0.2mmol,47mg)、N‑(新戊酰氧基)苯甲酰胺(0.3mmol,62mg)，DCE 2.0mL加入到15mL厚壁耐压管中，100℃下搅拌12小时，反应完毕后，用硅胶柱层析分离得到纯净的目标产物。本发明所提供的4‑炔基喹唑啉类化合物的制备方法具有科学合理、操作简单等特点。其反应方程式如下：
Description
技术领域
本发明属于有机合成技术领域，具体涉及一种4-炔基喹唑啉类化合物的制备方法。
背景技术
喹唑啉衍生物在有机合成和药物化学中都具有重要的应用价值。它们具有显著的生物活性，如抗惊厥、抗菌、抗糖尿病和抗癌等。在这类分子中，4-炔基喹唑啉已被证明是有效的杀菌剂，以及抗炎(J.Med.Chem.2006,49,6015)、抗癌(Bioorg.Med.Chem.2006,14,5020)、抗微生物(Biochemistry 2009,48,688)和抗高血压(J.Med.Chem.2007,50,182)的药物。
鉴于4-炔基喹唑啉化合物的广泛生物活性和应用价值，发展一种实用有效地合成4-炔基喹唑啉化合物的新方法具有重要意义。
4-炔基喹唑啉类化合物的制备方法有：
1)以末端炔和4-氯喹唑啉为原料
Sylvain Achelle课题组以末端炔和4-氯喹唑啉为原料，[Pd(PPh3)2Cl2]和CuI作催化剂、DIPA作溶剂、70℃条件下进行反应，制备4-芳炔基喹唑啉类衍生物(J.Org.Chem.2014,79,7564)。
2)以端炔和4-氯喹唑啉为原料
Kitano课题组以端炔和4-氯喹唑啉为原料，Pd(PPh3)4作催化剂、Et3N作碱、THF作溶剂，制备4-炔基喹唑啉类衍生物(Bioorg.Med.Chem.Lett.,2007,17,5863)。
3)以末端炔和4-(对甲苯磺酸基)喹唑啉为原料
彭以元课题组以末端炔和4-(对甲苯磺酸基)喹唑啉为原料，Pd(OAc)2作催化剂、DABCO作碱、DCE作溶剂、60℃条件下进行反应，制备4-炔基喹唑啉类衍生物(Org.Biomol.Chem.2014,12,5922)。
利用上述方法合成4-炔基喹唑啉类化合物，具有一定的缺点和不足：1)需要金属催化；2)操作繁琐。
发明内容
为了克服上述现有技术的不足，本发明提供了一种4-炔基喹唑啉类化合物的制备方法。
1.一种4-炔基喹唑啉类化合物的制备方法，所述4-炔基喹唑啉类化合物具有式I所示的结构：
式I中，其中R1选自氢、7-甲基、6-氟、6-氯；R2选自对甲基、对氟；R3选自间甲基、对氯、对氟、对三氟；其特征在于，向反应器中加入摩尔比为1：1.5的4-炔基苯并噁嗪与N-(新戊酰氧基)苯甲酰胺，加入DCE作为溶剂，100℃条件下搅拌反应，其化学过程见反应式Ⅱ：
本发明的有益效果为：本发明提供的4-炔基喹唑啉类化合物的合成方法科学合理，提供了一种合成多种取代基4-炔基喹唑啉类化合物的新途径；而且还具有原料易得、操作简单等特点。
附图说明
图1为实施例1制备的化合物3a的NMR图谱；
图2为实施例4制备的化合物3d的NMR图谱；
图3为实施例9制备的化合物3i的NMR图谱。
具体实施方式
下面结合附图和具体的实施例对本发明进一步详细的说明：
下述实施例中所述实验方法，如无特殊说明，均为常规方法；所述试剂和材料，如无特殊说明，均可从商业途径获得。
实施例1
4-炔基喹唑啉类化合物3a的制备
将4-苯乙炔基苯并噁嗪(0.2mmol,47mg)、N-(新戊酰氧基)苯甲酰胺(0.3mmol,62mg)，DCE 2.0mL加入到15mL厚壁耐压管中，100℃下搅拌12小时。反应完毕后，经柱层析分离(200-300目硅胶)(石油醚/乙酸乙酯＝70/1)得到2-苯基-4-(苯基乙炔基)喹唑啉3a(0.196mmol,60mg)，分离产率98％。
谱图解析数据3a:
1H NMR(500MHz,CDCl3):δ8.69–8.60(m,2H),8.40(ddd,J＝8.3,1.5,0.7Hz,1H),8.10(dt,J＝8.5,0.9Hz,1H),7.91(ddd,J＝8.4,6.9,1.5Hz,1H),7.83–7.74(m,2H),7.65(ddd,J＝8.2,6.9,1.2Hz,1H),7.58–7.50(m,3H),7.50–7.41(m,3H).13C NMR(101MHz,CDCl3):δ160.93,152.88,151.00,137.83,134.24,132.58,130.66,130.11,129.05,128.71,128.65,128.59,127.65,126.46,123.95,121.39,97.81,85.68.
实施例2
用1b代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3b:
1H NMR(500MHz,CDCl3):δ8.81–8.61(m,2H),8.29–8.15(m,1H),7.84–7.73(m,2H),7.71(dt,J＝7.0,1.3Hz,1H),7.58–7.48(m,4H),7.48–7.39(m,3H),2.86(s,3H).13C NMR(101MHz,CDCl3):δ159.66,152.83,149.98,138.14,137.50,134.00,132.55,130.52,129.98,128.67,128.62,128.53,127.22,124.12,123.87,121.53,97.26,86.03.
实施例3
用1c代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3c:
1H NMR(500MHz,CDCl3):δ8.70–8.54(m,2H),8.10(dd,J＝9.2,5.1Hz,1H),7.98(dd,J＝8.3,2.8Hz,1H),7.84–7.73(m,2H),7.67(ddd,J＝9.5,8.2,2.8Hz,1H),7.57–7.50(m,3H),7.50–7.40(m,3H).13C NMR(101MHz,CDCl3):δ160.76(1JC-F＝252.6Hz),160.55(4JC-F＝2.8Hz),152.34(3JC-F＝5.6Hz),148.19,137.52,132.61,131.80(3JC-F＝8.5Hz),130.74,130.28,128.69,128.63,128.58,124.62(2JC-F＝26.0Hz),124.51(3JC-F＝9.4Hz),121.12,109.86(2JC-F＝23.0Hz),98.27,85.25.
实施例4
用1d代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3d:
1H NMR(500MHz,CDCl3):δ8.62(dd,J＝7.4,2.5Hz,2H),8.33(d,J＝2.4Hz,1H),8.03(d,J＝8.9Hz,1H),7.80(ddd,J＝15.7,8.3,2.3Hz,3H),7.63–7.39(m,6H).13C NMR(101MHz,CDCl3):δ161.13,151.98,149.50,137.39,135.19,133.31,132.63,130.91,130.75,130.33,128.69,128.64,125.30,124.38,121.06,98.47,85.17.
实施例5
用1e代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3e:
1H NMR(500MHz,CDCl3):δ8.71–8.59(m,2H),8.38(dd,J＝8.3,1.3Hz,1H),8.08(d,J＝8.4Hz,1H),7.88(ddd,J＝8.4,6.8,1.5Hz,1H),7.70–7.58(m,3H),7.58–7.45(m,3H),7.24(d,J＝8.0Hz,2H),2.41(s,3H).13C NMR(101MHz,CDCl3):δ160.90,153.04,150.95,140.66,137.88,134.17,132.55,130.62,129.43,129.00,128.71,128.58,127.58,126.52,123.92,118.30,98.41,85.34,.
实施例6
用1f代替实例1中的1a，其他条件同实例1，实验结果见表1。
谱图解析数据3f:
1H NMR(500MHz,CDCl3):δ8.70–8.57(m,2H),8.36(dd,J＝8.3,1.4Hz,1H),8.10(d,J＝8.4Hz,1H),7.91(ddd,J＝8.5,6.9,1.5Hz,1H),7.81–7.72(m,2H),7.64(ddd,J＝8.1,6.8,1.2Hz,1H),7.58–7.48(m,3H),7.21–7.09(m,2H).13C NMR(101MHz,CDCl3):δ163.61(1JC-F＝252.6Hz),160.91,152.71,151.00,137.77,134.71(3JC-F＝8.7Hz),134.28,130.69,129.09,128.69,128.60,127.68,126.34,123.86,117.51(4JC-F＝3.6Hz),116.14(2JC-F＝22.3Hz),96.59,85.51,85.50.
实施例7
用2b代替实例1中的2a，其他条件同实例1，实验结果见表1。
谱图解析数据3g:
1H NMR(500MHz,CDCl3):δ8.65–8.55(m,2H),8.38(dd,J＝8.3,1.3Hz,1H),8.06(d,J＝8.4Hz,1H),7.90(ddd,J＝8.4,6.8,1.5Hz,1H),7.81–7.71(m,2H),7.65(ddd,J＝8.1,6.8,1.2Hz,1H),7.54–7.40(m,5H).13C NMR(101MHz,CDCl3):δ159.84,152.91,150.89,136.90,136.29,134.38,132.59,130.20,130.03,128.98,128.77,128.67,127.84,126.48,123.93,121.27,98.06,85.54.
实施例8
用2c代替实例1中的2a，其他条件同实例1，实验结果见表1。
谱图解析数据3h:
1H NMR(500MHz,CDCl3):δ8.71–8.60(m,2H),8.38(ddd,J＝8.3,1.5,0.7Hz,1H),8.07(dt,J＝8.5,0.9Hz,1H),7.90(ddd,J＝8.4,6.9,1.5Hz,1H),7.82–7.73(m,2H),7.64(ddd,J＝8.2,6.9,1.2Hz,1H),7.54–7.40(m,3H),7.24–7.14(m,2H).13C NMR(101MHz,CDCl3):δ164.74(1JC-F＝250.5Hz),159.95,152.89,150.94,134.34,133.99(4JC-F＝2.9Hz),132.58,130.82(3JC-F＝8.6Hz),130.17,128.93,128.67,127.67,126.48,123.82,121.30,115.51(2JC-F＝21.6Hz),97.94,85.58.
实施例9
用2d代替实例1中的2a，其他条件同实例1，实验结果见表1。
谱图解析数据3i:
1H NMR(500MHz,CDCl3):δ8.45(d,J＝11.1Hz,2H),8.39(d,J＝8.2Hz,1H),8.10(d,J＝8.5Hz,1H),7.95–7.85(m,1H),7.78(dd,J＝7.5,2.0Hz,2H),7.68–7.59(m,1H),7.44(dd,J＝14.9,7.3Hz,4H),7.32(d,J＝7.5Hz,1H),2.49(s,3H).13C NMR(101MHz,CDCl3):δ161.07,152.84,150.99,138.22,137.73,134.22,132.58,131.49,130.09,129.22,129.01,128.64,128.53,127.58,126.45,125.92,123.92,121.39,97.79,85.69,.
实施例10
用2e代替实例1中的2a，其他条件同实例1，实验结果见表1。
谱图解析数据3h:
1H NMR(500MHz,CDCl3):δ8.80–8.73(m,2H),8.44–8.36(m,1H),8.10(dt,J＝8.5,0.9Hz,1H),7.93(ddd,J＝8.4,6.9,1.4Hz,1H),7.78(dt,J＝7.7,1.4Hz,4H),7.68(ddd,J＝8.2,6.9,1.2Hz,1H),7.54–7.41(m,3H).13C NMR(101MHz,CDCl3):δ159.44,153.04,150.85,141.09,134.50,132.61,132.65(2JC-F＝32.3Hz),130.27,129.15,128.95,128.69,128.29,128.25,126.52,125.46(3JC-F＝3.8Hz),124.23(1JC-F＝273.3Hz),124.16,121.20,98.36,85.47.
表1
Claims (2)
1.一种4-炔基喹唑啉类化合物的制备方法，所述4-炔基喹唑啉类化合物具有式I所示的结构：
式I中，其中R1选自氢、7-甲基、6-氟、6-氯；R2选自对甲基、对氟；R3选自间甲基、对氯、对氟、对三氟；其特征在于，向反应器中加入摩尔比为1：1.5的4-炔基苯并噁嗪与N-(新戊酰氧基)苯甲酰胺，加入DCE作为溶剂，100℃条件下搅拌反应，其化学过程见反应式Ⅱ：
2.按照权利要求1所述的制备方法，其特征在于：DCE溶剂中加热反应12h。
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| WEN-KUI YUAN ET AL.: "A concise construction of 4-alkynylquinazolines via [4 + 2] annulation of 4-alkynylbenz-oxazinanones with acylhydroxamates under transition-metal-free conditions", 《ORG. CHEM. FRONT.》 * |
| YIYUAN PENG ET AL.: "Synthesis of 4-Alkynylquinazolines: Pd-Cu-cocatalyzed Coupling of Quinazoline-4-tosylates with Terminal Alkynes Using N-Heterocyclic Carbenes as Ligands", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 * |
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