CN112239426A - 一种n-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法 - Google Patents

一种n-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法 Download PDF

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CN112239426A
CN112239426A CN201911412635.1A CN201911412635A CN112239426A CN 112239426 A CN112239426 A CN 112239426A CN 201911412635 A CN201911412635 A CN 201911412635A CN 112239426 A CN112239426 A CN 112239426A
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quinoline
formamide
aroylmethylnaphthalene
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aryl
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金红蕾
黄乐浩
解春松
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Wenzhou Medical University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Abstract

本发明公开了一种N‑(2‑芳酰甲基萘)喹啉‑2‑甲酰胺类似物的制备方法，包括以下步骤：在钯催化剂和添加剂的作用下，N‑芳基‑喹啉‑2‑甲酰胺与α‑溴代芳基酮发生烷基化反应，得到N‑(2‑芳酰甲基萘)喹啉‑2‑甲酰胺类似物。该方法反应条件温和，得到的N‑(2‑芳酰甲基萘)喹啉‑2‑甲酰胺类似物可以具有多种官能团，是一种合成马兜铃内酰胺较好的原料。

Description

一种N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法
技术领域
本发明属于有机合成领域，具体涉及一种N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法。
背景技术
马兜铃内酰胺属于阿朴菲类生物碱的一种(式1)(Nat.Prod.Rep.2003,20,565-583)。研究表明，马兜铃内酰胺类生物碱具有良好的抗血小板凝聚(J.Nat.Prod.2000,63,1160-1163)、抗炎(Bioorg.Med.Chem.2007,15,988-996)、抗细菌(J.Nat.Prod.1992,55,1165-1169)等生物活性。
Figure BDA0002350379260000011
N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物可以用来合成马兜铃内酰胺，反应方式如下：
Figure BDA0002350379260000012
通过该方法合成马兜铃内酰胺，操作过程简单，因此，开发出一种有效合成N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的方法具有重要的意义。
发明内容
本发明提供了一种N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，该制备方法操作条件简单，制备得到的产物中官能团容忍性好，可以用于合成多种马兜铃内酰胺。
一种N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，包括以下步骤：
在钯催化剂和添加剂的作用下，N-芳基-喹啉-2-甲酰胺与α-溴代芳基酮发生烷基化反应，得到所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物；
所述的N-芳基-喹啉-2-甲酰胺的结构如式(II)所示：
Figure BDA0002350379260000021
所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的结构如式(I)所示：
Figure BDA0002350379260000022
Ar为取代或者未取代的芳基；
所述芳基上的取代基为C1～C5烷基、C1～C5烷氧基、卤素或-CF3中的一种或者多种。
作为优选，所述的Ar为取代或者未取代的苯基，所述苯基上的取代基为甲基、甲氧基、F、Cl、Br、-CF3中的一种或者多种。
作为优选，所述的钯催化剂为醋酸钯、PdCl2、Pd(PPh3)4和Pd2(dba)3中的一种或者多种。
作为优选，所述的添加剂为PhCOOK、NaOAc和K2CO3中的至少一种。
作为优选，所述的烷基化反应的溶剂为1,2-二氯乙烷、1,4-二氧六环、叔丁醇中的至少一种。
作为最优选，所述的钯催化剂为醋酸钯，所述的添加剂为PhCOOK，所述的烷基化反应的溶剂为1,2-二氯乙烷，此时，反应的收率最高。
作为优选，所述的烷基化反应的温度为80～100℃，反应时间为8～24小时。
同现有技术相比，本发明的有益效果体现在：
本发明的制备方法反应条件温和，底物的官能团容忍性好，能用于合成多种不同的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物，进而可以用于合成马兜铃内酰胺。
具体实施方式
实施例1
将喹啉-2-甲酸(20mmol)，萘-1-胺(20mmol,2.86g)和Et3N(40mmol,5.6mL)溶解在CH2Cl2(40mL)中，然后在0℃滴加POCl3(3.76mL)。反应混合物在0℃搅拌0.5h。然后，在室温下继续反应2h直到萘-1-胺消耗完。在反应结束后，反应混合物冷却至0℃，缓慢加入冰水淬灭反应。收集有机相，水相用CH2Cl2(3×20mL)萃取。合并有机相，用饱和的NaHCO3水溶液(2×40mL)洗涤，无水MgSO4干燥。减压蒸去溶剂，残余物用CH2Cl2/石油醚进行结晶，得到目标化合物。
反应式如下：
Figure BDA0002350379260000031
产物表征数据如下：
N-(Naphthalen-1-yl)quinoline-2-carboxamide(II-1,CAS no.298193-67-6):4.29g,收率：72％；粉红色固体；mp＝146-147℃；1H NMR(400MHz,CDCl3)δ10.95(s,1H),8.43(d,J＝8.4Hz,2H),8.36(d,J＝8.0Hz,1H),8.25(d,J＝8.4Hz,1H),8.16(d,J＝8.4Hz,1H),7.91(d,J＝8.0Hz,2H),7.81(t,J＝7.2Hz,1H),7.71(d,J＝8.4Hz,1H),7.59(m,4H)；13C NMR(100MHz,CDCl3)δ162.4,149.9,146.3,138.0,134.2,132.5,130.4,129.9,129.5,128.9,128.2,127.9,126.5,126.3,126.1,126.0,125.1,120.5,118.8,118.7；HRMS(ESI)calcdfor C20H14N2O[M+H]+299.1179,found 299.1182。
实施例2
在空气氛围下，将酰胺II-1(0.25mmol,1.0equiv)，α-溴代酮III-1(0.5mmol,2.0equiv),催化剂(0.025mmol,10mol％),添加剂(0.25mmol,1.0equiv)和溶剂(2.0mL)加入35mL带聚四氟乙烯帽的压力反应管中。将反应管在指定温度下反应若干小时，然后将反应混合物冷却至室温，用乙酸乙酯(5mL)稀释，硅藻土过滤，减压浓缩，残余物用硅胶柱色谱纯化(洗脱剂为乙酸乙酯/石油醚)得到目标产物I-1。反应条件和反应结果列于表1。
表1实施例2的反应条件和反应结果
Figure BDA0002350379260000041
实施例3化合物I的制备
在空气氛围下，将酰胺II-1(0.25mmol,1.0equiv)，α-溴代酮III(0.5mmol,2.0equiv),Pd(OAc)2(0.025mmol,10mol％),PhCOOK(0.25mmol,1.0equiv)和1,2-二氯乙烷(2.0mL)加入35mL带聚四氟乙烯帽的压力反应管中。将反应管在50或70℃下反应12小时，然后将反应混合物冷却至室温，用乙酸乙酯(5mL)稀释，硅藻土过滤，减压浓缩，残余物用硅胶柱色谱纯化(洗脱剂为乙酸乙酯/石油醚)得到目标产物。反应条件和反应结果列于表2。
表2实施例3的反应条件和反应结果
Figure BDA0002350379260000051
[a]1a(0.25mmol,75mg),Pd(OAc)2(0.025mmol,6mg),α-溴代酮(0.5mmol),PhCOOK(0.25mmol,40mg),DCE(2mL),70℃,12h.
[b]基于II-1的分离收率。
[c]3.34mmol当量的分离收率。
[d]50℃下反应。
产物的结构和表征数据如下：
Figure BDA0002350379260000061
N-(8-(2-oxo-2-phenylethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-1):85mg,82％收率；棕色固体；柱分离洗脱剂：乙酸乙酯/石油醚＝1/4,v/v)；mp＝146-147℃.1H NMR(600MHz,CDCl3)δ10.31(s,1H),8.25(d,J＝7.8Hz,1H),8.18(d,J＝9.0Hz,1H),7.88(t,J＝8.4Hz,2H),7.77(m,3H),7.71(d,J＝7.2Hz,1H),7.54(m,4H),7.42(t,J＝7.2Hz,1H),7.26(d,J＝6.6Hz,1H),7.07(t,J＝7.2,1H),6.97(t,J＝7.8Hz,2H),4.93(s,2H)；13C NMR(150MHz,CDCl3)δ198.9,164.2,149.4,146.1,137.5,136.5,136.2,132.5,131.6,130.1,130.0,129.9,129.8,129.3,129.2,129.1,128.2,128.1,128.0,127.9,127.5,127.3,125.6,125.5,118.9,46.4.HRMS(ESI)calcd for C28H20N2O2[M+H]+417.1598,found417.1589.
Figure BDA0002350379260000062
N-(8-(2-oxo-2-(p-tolyl)ethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-2):85mg,79％收率；棕色固体；柱分离洗脱剂：乙酸乙酯/石油醚＝1/4,v/v)；mp＝164-165℃.1H NMR(500MHz,CDCl3)δ10.26(s,1H),8.25(d,J＝8.0Hz,1H),8.19(d,J＝8.5Hz,1H),7.87(t,J＝8.5Hz,2H),7.77(d,J＝8.0Hz,1H),7.65(d,J＝7.5Hz,3H),7.53(m,4H),7.42(t,J＝7.5Hz,1H),7.25(d,J＝6.5Hz,1H),6.71(d,J＝8.0Hz,2H),4.88(s,2H),2.02(s,3H)；13C NMR(125MHz,CDCl3)δ198.2,164.2,149.5,146.1,143.3,137.2,136.1,134.0,132.5,131.5,130.1,130.0,129.9,129.5,129.2,129.0,128.8,128.1,127.8,127.3,127.2,125.4,118.8,46.1,21.3；HRMS(ESI)calcd for C29H22N2O2[M+H]+431.1754,found431.1741.
Figure BDA0002350379260000071
N-(8-(2-(4-methoxyphenyl)-2-oxoethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-3):71mg,64％收率；棕色固体；柱分离洗脱剂：二氯甲烷/石油醚＝1/3,v/v)；mp＝120-121℃；1H NMR(600MHz,CDCl3)δ10.31(s,1H),8.26(d,J＝8.4Hz,1H),8.20(d,J＝8.4Hz,1H),7.87(t,J＝8.4Hz,2H),7.79(d,J＝7.2Hz,1H),7.74(d,J＝9.0Hz,2H),7.68(d,J＝7.8Hz,1H),7.56(m,4H),7.42(t,J＝7.2Hz,1H),7.26(d,J＝6.6Hz,1H),6.40(d,J＝8.4Hz,2H),4.86(s,2H),3.75(s,3H)；13C NMR(150MHz,CDCl3)δ197.3,164.3,163.1,149.6,146.2,137.4,136.2,132.5,131.6,130.3,130.2,130.1,129.7,129.6,129.3,129.2,129.1,127.9,127.4,125.5,119.0,113.3,55.3,46.0；HRMS(ESI)calcd for C29H22N2O3[M+H]+447.1703,found 447.1691.
Figure BDA0002350379260000072
N-(8-(2-(3-methoxyphenyl)-2-oxoethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-4):61mg,55％收率；棕色固体；柱分离洗脱剂：二氯甲烷/石油醚＝1/3,v/v)；mp＝148-149℃.1H NMR(500MHz,CDCl3)δ10.25(s,1H),8.25(d,J＝8.5Hz,1H),8.19(d,J＝8.5Hz,1H),7.88(t,J＝7.0Hz,2H),7.77(d,J＝7.5Hz,1H),7.68(d,J＝7.5Hz,1H),7.56(m,4H),7.42(t,J＝7.5Hz,1H),7.31(s,2H),7.25(s,1H),6.80(t,J＝8.0Hz,1H),6.55(d,J＝7.5Hz,1H),4.90(s,2H),3.61(s,3H)；13C NMR(125MHz,CDCl3)δ198.3,164.1,159.3,149.4,146.0,137.8,137.3,136.1,132.4,131.5,130.0,129.9,129.8,129.6,129.2,129.1,129.0,128.9,127.8,127.3,127.2,125.4,125.3,120.5,118.7,112.3,55.1,46.4；HRMS(ESI)calcd for C29H22N2O3[M+H]+447.1703,found 447.1691.
Figure BDA0002350379260000081
N-(8-(2-(2-methoxyphenyl)-2-oxoethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-5):85mg,76％收率；棕色固体；柱分离洗脱剂：乙酸乙酯/石油醚/二氯甲烷＝1/6/0.04,v/v/v)；mp＝147-148℃.1H NMR(500MHz,CDCl3)δ10.43(s,1H),8.30(d,J＝8.0Hz,1H),8.22(d,J＝9.0Hz,1H),7.84(m,3H),7.77(d,J＝7.5Hz,2H),7.54(t,J＝7.5Hz,1H),7.45(m,3H),7.39(t,J＝7.0Hz,1H),7.20(d,J＝6.5Hz,1H),7.08(t,J＝8.5Hz,1H),6.81(t,J＝7.5Hz,1H),6.27(d,J＝9.0Hz,1H),4.92(s,2H),3.21(s,3H)；13C NMR(125MHz,CDCl3)δ200.8,163.6,158.6,149.7,146.1,137.1,136.0,133.5,132.5,131.0,130.9,129.9,129.7,129.6,129.0,128.9,128.6,127.8,127.6,127.2,126.6,125.4,125.3,120.4,118.7,110.8,54.7,52.1；HRMS(ESI)calcd for C29H22N2O3[M+H]+447.1703,found447.1691.
Figure BDA0002350379260000082
N-(8-(2-(4-bromophenyl)-2-oxoethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-6):86mg,70％收率；棕色固体；柱分离洗脱剂：乙酸乙酯/石油醚/二氯甲烷＝1/8/0.04,v/v/v)；mp＝180-181℃；1H NMR(500MHz,CDCl3)δ10.10(s,1H),8.21(d,J＝8.5Hz,1H),8.19(d,J＝8.5Hz,1H),7.88(t,J＝7.0Hz,2H),7.82(d,J＝7.5Hz,1H),7.59(m,7H),7.43(t,J＝7.5Hz,1H),7.24(d,J＝7.0Hz,1H),6.96(d,J＝6.5Hz,2H),4.83(s,2H)；13CNMR(125MHz,CDCl3)δ197.1,164.1,149.2,146.0,137.5,136.1,135.0,132.2,131.7,131.2,130.1,130.0,129.5,129.4,129.3,129.2,129.1,128.2,127.8,127.7,127.5,125.5,125.4,118.7,46.5；HRMS(ESI)calcd for C28H19BrN2O2[M+H]+495.0703,found495.0708.
Figure BDA0002350379260000091
N-(8-(2-(4-chlorophenyl)-2-oxoethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-7):88mg,78％收率；棕色固体；柱分离洗脱剂：二氯甲烷/石油醚＝1/3,v/v)；mp＝181-182℃；1H NMR(500MHz,CDCl3)δ10.11(s,1H),8.21(s,2H),7.89(t,J＝7.5Hz,2H),7.82(t,J＝7.5Hz,1H),7.61(m,6H),7.54(t,J＝8.0Hz,1H),7.43(t,J＝7.0Hz,1H),7.25(d,J＝6.0Hz,1H),6.82(d,J＝9.0Hz,2H),4.85(s,2H)；13C NMR(125MHz,CDCl3)δ197.0,164.1,149.2,146.0,139.0,137.4,136.1,134.7,132.3,131.6,130.1,129.9,129.5,129.4,129.3,129.2,129.1,128.2,128.1,127.6,127.4,125.5,125.4,118.7,46.4；HRMS(ESI)calcd for C28H19ClN2O2[M+H]+451.1208,found451.1184.
Figure BDA0002350379260000092
N-(8-(2-(4-fluorophenyl)-2-oxoethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-8):77mg,71％收率；棕色固体；柱分离洗脱剂：二氯甲烷/石油醚＝1/3,v/v)；mp＝185-186℃；1H NMR(500MHz,CDCl3)δ10.18(s,1H),8.24(d,J＝8.5Hz,1H),8.20(d,J＝8.5Hz,1H),7.88(t,J＝7.0Hz,2H),7.80(d,J＝7.5Hz,1H),7.75(t,J＝6.0Hz,2H),7.67(d,J＝7.0Hz,1H),7.61(m,3H),7.54(t,J＝8.5Hz,1H),7.42(d,J＝7.5Hz,1H),7.25(d,J＝7.0Hz,1H),6.56(t,J＝8.0Hz,2H),4.87(s,2H)；13C NMR(125MHz,CDCl3)δ196.8,165.2(d,J＝253.0Hz),164.0,149.4,146.0,137.4,136.1,132.9(d,J＝2.9Hz),132.4,131.5,130.5,130.4,130.0,129.8,129.6,129.5,129.3,129.1,129.0,128.1,127.5,127.3,125.4(d,J＝7.9Hz),118.8,115.0(d,J＝21.5Hz),46.3；HRMS(ESI)calcd for C28H19FN2O2[M+H]+435.1503,found435.1504.
Figure BDA0002350379260000101
N-(8-(2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)naphthalen-1-yl)quinoline-2-carboxamide(I-9):63mg,52％收率；棕色固体；柱分离洗脱剂：二氯甲烷/石油醚＝1/3,v/v；mp＝178-179℃；1H NMR(500MHz,CDCl3)δ10.07(s,1H),8.18(d,J＝8.5Hz,1H),8.14(d,J＝8.5Hz,1H),7.90(dd,J＝8.0,3.5Hz,2H),7.76(m,3H),7.64(d,J＝7.0Hz,1H),7.57(m,4H),7.44(t,J＝7.5Hz,1H),7.26(d,J＝6.0Hz,1H),7.08(d,J＝8.0Hz,2H),4.90(s,2H)；13C NMR(125MHz,CDCl3)δ197.0,164.0,149.1,145.8,138.9,137.5,136.1,133.5(q,J＝32.8Hz),132.2,131.7,130.1,130.0,129.5,129.3,129.2,129.1,129.0,128.2,128.1,127.6,127.5,125.5,125.4,124.9(q,J＝3.6Hz),123.2(q,J＝270.6Hz),118.6,46.9；HRMS(ESI)calcd for C29H19F3N2O2[M+H]+485.1471,found 485.1439.
Figure BDA0002350379260000102
N-(8-(2-oxopropyl)naphthalen-1-yl)quinoline-2-carboxamide(I-10):50mg,56％收率；棕色固体；柱分离洗脱剂：乙酸乙酯/石油醚＝1/6,v/v)；mp＝179-180℃；1H NMR(600MHz,CDCl3)δ10.52(s,1H),8.44(d,J＝7.8Hz,1H),8.39(d,J＝8.4Hz,1H),8.19(d,J＝8.4Hz,1H),7.94(d,J＝8.4Hz,1H),7.85(d,J＝8.4Hz,2H),7.81(t,J＝7.2Hz,1H),7.75(d,J＝7.2Hz,1H),7.67(t,J＝7.2Hz,1H),7.54(t,J＝7.8Hz,1H),7.41(t,J＝7.8Hz,1H),7.23(d,J＝7.8Hz,1H),4.41(s,2H),2.11(s,3H)；13C NMR(150MHz,CDCl3)δ208.0,164.0,150.0,146.6,137.9,137.8,136.2,132.5,131.3,130.5,129.9,129.6,129.5,128.8,128.4,128.0,127.2,125.7,125.5,119.3,51.2,30.4；HRMS(ESI)calcd for C23H18N2O2[M+H]+355.1441,found 355.1444。

Claims (7)

1.一种N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，包括以下步骤：
在钯催化剂和添加剂的作用下，N-芳基-喹啉-2-甲酰胺与α-溴代芳基酮发生烷基化反应，得到所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物；
所述的N-芳基-喹啉-2-甲酰胺的结构如式(II)所示：
Figure FDA0002350379250000011
所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的结构如式(III)所示：
Figure FDA0002350379250000012
Ar为取代或者未取代的芳基；
所述芳基上的取代基为C1～C5烷基、C1～C5烷氧基、卤素或-CF3中的一种或者多种。
2.根据权利要求1所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，所述的Ar为取代或者未取代的苯基，所述苯基上的取代基为甲基、甲氧基、F、Cl、Br、-CF3中的一种或者多种。
3.根据权利要求1所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，所述的钯催化剂为醋酸钯、PdCl2、Pd(PPh3)4和Pd2(dba)3中的一种或者多种。
4.根据权利要求1所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，所述的添加剂为PhCOOK、NaOAc和K2CO3中的至少一种。
5.根据权利要求1所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，所述的烷基化反应的溶剂为1,2-二氯乙烷、1,4-二氧六环、叔丁醇中的至少一种。
6.根据权利要求1所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，所述的钯催化剂为醋酸钯，所述的添加剂为PhCOOK，所述的烷基化反应的溶剂为1,2-二氯乙烷。
7.根据权利要求1所述的N-(2-芳酰甲基萘)喹啉-2-甲酰胺类似物的制备方法，其特征在于，所述的烷基化反应的温度为80～100℃，反应时间为8～24小时。
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