CN113372298B - 一种2-碘-3-胺基萘醌化合物的制备方法 - Google Patents
一种2-碘-3-胺基萘醌化合物的制备方法 Download PDFInfo
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Abstract
本发明涉及一种2‑碘‑3‑胺基萘醌化合物的制备方法,在有机溶剂中,氮气条件下,以N‑碘代丁二酰亚胺、仲胺和萘醌为反应原料,利用原位生成的碘胺化试剂,通过自由基串联反应得到2‑碘‑3‑胺基萘醌化合物。所述方法反应条件简单、产物的产率和纯度高,为2‑碘‑3‑胺基萘醌化合物的制备开拓了合成路线和方法,具有良好的应用潜力和研究价值。
Description
技术领域
本发明属于有机化合物合成技术领域,尤其是涉及一种2-碘-3-胺基萘醌化合物的制备方法。
背景技术
2-胺基-3-取代萘醌作为核心骨架广泛存在于具有重要生物活性的天然产物、抗生素、抗氧化药物分子和候选抗癌药物中,例如:抗生素mevashuntin、抗肿瘤药物griffithazanoneA、人DNA拓扑异构酶抑制剂calothrixin B和除草剂灭澡醌(Org.Lett.2012,14,1484-1487;J.Nat.Prod.2003,66,487-490;Org.Lett.2006,8,561-564;Biochem.Pharmacol.1997,54,259-268.)。当前发展的合成此类化合物方法都依赖于预官能团化合成砌块的操作(Russ.Chem.B.2012,61,582-588;J.Org.Chem.2014,79,2331-2336;Tetrahedron Lett.2015,56,6273-6275;Tetrahedron Lett.2018,59,438-441;Eur.J.Med.Chem.2018,156,1-12;J.Org.Chem.2019,84,1006-1014.),存在官能团兼容性差,合成步骤繁琐,不利于药物分子后期修饰等缺点,发展萘醌的直接双官能团方法可以使合成更加线性化,为复杂小分子的后期修饰提供强有力的工具。
含2-胺基-3-取代萘醌结构的药物和活性分子:
值得一提的是,2-碘-3-胺基萘醌化合物的合成方法至今未见报道,从而抑制了此类化合物在药物化学领域的研究和萘醌创新药物的发现机会。最近,我们课题组利用原位生成的胺卤化试剂作为双官能团化试剂,实现了铜催化马来酰亚胺的胺卤化反应(OrganicLetters,2021,23,3669-3673)。考虑到萘醌结构修饰在创新药物研发中的重要性,利用简便、易于处理的实验操作条件、底物廉价易得的原料来制备2-碘-3-胺基萘醌化合物的反应显得尤为重要,这是本发明得以完成的基础和动力所在。
发明内容
本发明所要解决的技术问题是2-碘-3-胺基萘醌化合物的制备方法的合成路线问题。
为解决以上技术问题,本发明提供下述技术方案:
一种2-碘-3-胺基萘醌化合物的制备方法,在有机溶剂中,氮气条件下,以N-碘代丁二酰亚胺、仲胺和萘醌为反应原料,利用原位生成的碘胺化试剂,通过自由基串联反应得到2-碘-3-胺基萘醌化合物;
上述的反应过程,可用下述的反应式表示:
所述N-碘代丁二酰亚胺、仲胺和萘醌的摩尔比为3∶3∶1。
(1)有机溶剂
本发明中的反应溶剂为有机溶剂,所述有机溶剂为二甲基亚砜、N,N-二甲基甲酰胺、1,4-二氧六烷、1,2-二氯乙烷、乙腈、甲苯、四氢呋喃中的至少一种,优选乙腈。
(2)反应温度
本发明的制备方法中,反应温度为室温25℃。
(3)反应时间
在本发明的制备方法中,反应时间为2分钟。
(5)分离纯化
在一种优选的实施方式中,反应结束后的后处理步骤可为如下方法:反应结束后,将反应液冷却后加入乙酸乙酯稀释,将有机相过滤至鸡心瓶,然后旋掉溶剂,将浓缩物通过柱色谱分离,以石油醚和乙酸乙酯混合液为洗脱剂,收集洗脱液,浓缩后得到目标产物。
本发明提供的2-碘-3-胺基萘醌化合物的制备方法具有如下有益效果:
a)反应条件温和,快速;
b)利用原位生成的碘胺化试剂为双官能团化试剂;
c)实验操作简单,产率产率高;
本发明以N-碘代丁二酰亚胺、仲胺和萘醌为反应原料,氮气条件下,利用原位生成的碘胺化试剂,通过自由基串联反应得到2-碘-3-胺基萘醌化合物。本发明反应原料廉价易得、产物的产率和纯度高,为2-碘-3-胺基萘醌化合物的制备开拓了合成路线和方法,为双取代马来酰亚胺衍生物的分子设计与合成提供新思路,具有重要的社会意义和经济意义。
具体实施方式
下面通过具体的实施例对本发明进行详细说明,但这些例举性实施方式的用途和目的仅用来例举本发明,并非对本发明的实际保护范围构成任何形式的任何限定,更非将本发明的保护范围局限于此。
以下实施例所给出的新化合物的数据和纯度均通过核磁共振鉴定。
实施1:
2-碘-3-吗啉基萘醌化合物的合成
在室温下,将萘醌(0.2mmol,1.0equiv)、N-碘代丁二酰亚胺(0.6mmol,3.0equiv)和2mL乙腈加入到反应管中,然后加入吗啉(0.6mmol,3.0equiv)、抽气-充氮气置换三次,室温搅拌2分钟。加入乙酸乙酯进行稀释,将有机相过滤至鸡心瓶,旋掉有机溶剂,经柱层析分离得到产物(洗脱剂:石油醚∶乙酸乙酯为9∶1),产物为紫黑色固体,熔点为90-91℃,收率97%,产物重量为71mg。
所得产物的核磁共振氢谱的数据如下:
1H NMR(400MHz,CDCl3):δ8.12(dd,J=7.3,1.7Hz,1H),8.02(dd,J=7.3,1.7Hz,1H),7.69(pd,J=7.4,1.6Hz,2H),3.91(t,J=4.5Hz,4H),3.65(t,J=4.5Hz,4H);
所得产物的核磁共振碳谱的数据如下:
13C NMR(100MHz,CDCl3):δ180.8,179.7,157.9,134.0,133.3,131.4,130.1,127.5,127.1,102.5,67.6,52.7;所得产物的高分辨质谱数据如下:
HRMS(ESI):calcd for C14H13NO3I[M+H]+369.9940,found 369.9941.
实施2:
2-碘-3-(顺式-2,6-二甲基吗啉基)萘醌化合物的合成
在室温下,将萘醌(0.2mmol,1.0equiv)、N-碘代丁二酰亚胺(0.6mmol,3.0equiv)和2mL乙腈加入到反应管中,然后加入顺式-2,6-二甲基吗啉(0.6mmol,3.0equiv)、抽气-充氮气置换三次,室温搅拌2分钟。加入乙酸乙酯进行稀释,将有机相过滤至鸡心瓶,旋掉有机溶剂,经柱层析分离得到产物(洗脱剂:石油醚∶乙酸乙酯为9∶1),产物为紫黑色固体,熔点为126-127℃,收率94%,产物重量为74mg。
所得产物的核磁共振氢谱的数据如下:
1H NMR(400MHz,CDCl3):δ8.12(dd,J=7.3,1.7Hz,1H),8.02(dd,J=7.3,1.7Hz,1H),7.69(pd,J=7.4,1.6Hz,2H),3.96(ddt,J=12.6,6.3,3.2Hz,2H),3.65(d,J=12.9Hz,2H),3.16(dd,J=13.0,10.2Hz,2H),1.24(d,J=6.3Hz,6H);
所得产物的核磁共振碳谱的数据如下:
13C NMR(100MHz,CDCl3):δ180.9,179.7,157.5,134.0,133.2,131.4,130.1,127.5,127.1,101.4,72.4,57.7,18.6;
所得产物的高分辨质谱数据如下:
HRMS(ESI):calcd for C16H16NO3NaI[M+Na]+420.0073,found 420.0079.
实施3:
2-碘-3-(3-哌啶甲酸乙酯基)萘醌化合物的合成
在室温下,将萘醌(0.2mmol,1.0equiv)、N-碘代丁二酰亚胺(0.6mmol,3.0equiv)和2mL乙腈加入到反应管中,然后加入3-哌啶甲酸乙酯(0.6mmol,3.0equiv)、抽气-充氮气置换三次,室温搅拌2分钟。加入乙酸乙酯进行稀释,将有机相过滤至鸡心瓶,旋掉有机溶剂,经柱层析分离得到产物(洗脱剂:石油醚∶乙酸乙酯为9∶1),产物为紫黑色液体,收率93%,产物重量为81mg。
所得产物的核磁共振氢谱的数据如下:
1H NMR(400MHz,CDCl3):δ8.08(dd,J=7.3,1.7Hz,1H),8.00(dd,J=7.3,1.7Hz,1H),7.67(pd,J=7.4,1.6Hz,2H),4.15(q,J=7.1Hz,2H),3.92-3.88(m,1H),3.59(dt,J=13.4,4.0Hz,1H),3.51-3.37(m,2H),2.88(ddt,J=14.0,9.3,4.0Hz,1H),2.14(dd,J=9.3,5.0Hz,1H),1.94(dq,J=11.0,6.7,5.1Hz,1H),1.80(t,J=9.3Hz,2H),1.25(t,J=7.1Hz,3H);
所得产物的核磁共振碳谱的数据如下:
13C NMR(100MHz,CDCl3):δ180.7,179.7,173.2,158.9,133.9,133.2,131.5,130.1,127.4,127.1,103.3,60.7,54.3,53.2,42.2,26.8,25.2,14.3;
所得产物的高分辨质谱数据如下:
HRMS(ESI):calcd for C18H18NO4NaI[M+Na]+462.0178,found 462.0180.
实施4:
2-碘-3-(1-叔丁氧羰基哌嗪基)萘醌化合物的合成
在室温下,将萘醌(0.2mmol,1.0equiv)、N-碘代丁二酰亚胺(0.6mmol,3.0equiv)和2mL乙腈加入到反应管中,然后加入1-叔丁氧羰基哌嗪(0.6mmol,3.0equiv)、抽气-充氮气置换三次,室温搅拌2分钟。加入乙酸乙酯进行稀释,将有机相过滤至鸡心瓶,旋掉有机溶剂,经柱层析分离得到产物(洗脱剂:石油醚∶乙酸乙酯为9∶1),产物为紫黑色液体,收率85%,产物重量为79mg。
所得产物的核磁共振氢谱的数据如下:
1H NMR(400MHz,CDCl3):δ8.10(dd,J=7.3,1.7Hz,1H),8.01(dd,J=7.3,1.7Hz,1H),7.68(pd,J=7.4,1.6Hz,2H),3.66(t,J=4.7Hz,4H),3.56(t,J=4.7Hz,4H),1.51(s,9H);
所得产物的核磁共振碳谱的数据如下:
13C NMR(100MHz,CDCl3):δ180.7,179.7,158.3,154.8,134.0,133.3,131.4,130.0,127.4,127.2,103.8,80.2,52.1,28.5,26.9;
所得产物的高分辨质谱数据如下:
HRMS(ESI):calcd for C19H21N2O4NaI[M+Na]+491.0444,found 491.0443.
实施5:
2-碘-3-(1-乙酰哌嗪基)萘醌化合物的合成
在室温下,将萘醌(0.2mmol,1.0equiv)、N-碘代丁二酰亚胺(0.6mmol,3.0equiv)和2mL乙腈加入到反应管中,然后加入1-乙酰哌嗪(0.6mmol,3.0equiv)、抽气-充氮气置换三次,室温搅拌2分钟。加入乙酸乙酯进行稀释,将有机相过滤至鸡心瓶,旋掉有机溶剂,经柱层析分离得到产物(洗脱剂:石油醚∶乙酸乙酯为9∶1),产物为紫黑色液体,收率89%,产物重量为73mg。
所得产物的核磁共振氢谱的数据如下:
1H NMR(400MHz,CDCl3):δ8.08(dd,J=7.3,1.7Hz,1H),8.00(dd,J=7.3,1.7Hz,1H),7.68(pd,J=7.4,1.6Hz,2H),3.83(dd,J=6.5,3.7Hz,2H),3.69(dd,J=6.5,3.4Hz,2H),3.59(dd,J=6.3,3.4Hz,2H),3.54(dd,J=6.1,3.8Hz,2H),2.16(s,3H);
所得产物的核磁共振碳谱的数据如下:
13C NMR(100MHz,CDCl3):δ180.6,179.6,169.2,158.2,134.1,133.5,131.4,130.0,127.5,127.2,105.1,52.1,52.0,47.1,42.2,21.5;
所得产物的高分辨质谱数据如下:
HRMS(ESI):calcd for C16H15N2O3NaI[M+Na]+433.0025,found 433.0031.
实施6:
2-碘-3-(1-(2-嘧啶基)哌嗪基)萘醌化合物的合成
在室温下,将萘醌(0.2mmol,1.0equiv)、N-碘代丁二酰亚胺(0.6mmol,3.0equiv)和2mL乙腈加入到反应管中,然后加入1-(2-嘧啶基)哌嗪(0.6mmol,3.0equiv)、抽气-充氮气置换三次,室温搅拌2分钟。加入乙酸乙酯进行稀释,将有机相过滤至鸡心瓶,旋掉有机溶剂,经柱层析分离得到产物(洗脱剂:石油醚∶乙酸乙酯为9∶1),产物为紫黑色液体,收率82%,产物重量为73mg。
所得产物的核磁共振氢谱的数据如下:
1H NMR(400MHz,CDCl3):δ8.38(d,J=4.8Hz,2H),8.14(dd,J=7.3,1.7Hz,1H),8.06(dd,J=7.3,1.7Hz,1H),7.70(pd,J=7.4,1.6Hz,2H),6.58(t,J=4.8Hz,1H),4.10(t,J=4.7Hz,4H),3.70(t,J=4.7Hz,4H);
所得产物的核磁共振碳谱的数据如下:
13C NMR(100MHz,CDCl3):δ180.8,179.7,161.4,158.4,157.8,134.0,133.3,131.5,130.1,127.5,127.2,110.3,103.1,52.2,44.7;
所得产物的高分辨质谱数据如下:
HRMS(ESI):calcd for C18H16N4O2I[M+H]+447.0318,found 447.0324.
由上述实施例1-6可看出,当采用本发明的所述方法时,能够以高产率、高纯度得到2-碘-3-胺基萘醌化合物。
实施例7-12
除将其中的有机溶剂乙腈分别替换为如下的有机溶剂外,以与实施例1相同的方式而分别实施了实施7-12,所使用有机溶剂和相应产物的收率如下表2所示。
表2
编号 | 溶剂 | 反应产率(%) |
实施例7 | N,N-二甲基甲酰胺 | 21 |
实施例8 | 二甲亚砜 | 33 |
实施例9 | 1,4-二氧六烷 | 81 |
实施例10 | 1,2-二氯乙烷 | 61 |
实施例11 | 甲苯 | 94 |
实施例12 | 四氢呋喃 | 72 |
由上表2可看出,反应对反应溶剂不是很敏感,无论是强极性溶剂还是非极性溶剂,均能够顺利地进行,但是在甲苯溶剂中能够得到很完美的产率外,使用其他溶剂时,反应产率相对较低。
综上所述,由上述所有实施例可明确看出,当采用本发明的方法使用合适的有机溶剂乙腈时,使得N-碘代丁二酰亚胺、仲胺和萘醌,在氮气条件下,利用原位生成的碘胺化试剂,通过自由基串联反应以高产率和高纯度合成得到2-碘-3-胺基萘醌化合物,为该类化合物的高效快捷合成提供了全新的合成路线。
最后应说明的是:以上各实施例仅用以说明本发明的技术方案,而非对其限制;尽管参照前述各实施例对本发明进行了详细的说明,本领域的普通技术人员应当理解:其依然科研对前述各实施例所记载的技术方案进行修改,或者对其中部分或者全部技术特征进行等同替换;而这些修改或者替换,并不使相应技术方案的本质脱离本发明各实施例技术方案的范围。
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