CN106478507A - 一种2‑(1,3,5‑三芳基‑1‑h‑吡唑‑4‑基)丙二腈的制备方法 - Google Patents
一种2‑(1,3,5‑三芳基‑1‑h‑吡唑‑4‑基)丙二腈的制备方法 Download PDFInfo
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- CNKWKSWNZJWVGC-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1-c1c(C(C#N)C#N)c(-c2ccccc2)n[n]1-c(cc1)ccc1Br Chemical compound CC(C)(C)c(cc1)ccc1-c1c(C(C#N)C#N)c(-c2ccccc2)n[n]1-c(cc1)ccc1Br CNKWKSWNZJWVGC-UHFFFAOYSA-N 0.000 description 1
- YKAFSDGLJLMNKH-UHFFFAOYSA-N Cc(cc1)ccc1-c(c(C(C#N)C#N)c1-c2cc(Cl)ccc2)n[n]1-c1ccccc1 Chemical compound Cc(cc1)ccc1-c(c(C(C#N)C#N)c1-c2cc(Cl)ccc2)n[n]1-c1ccccc1 YKAFSDGLJLMNKH-UHFFFAOYSA-N 0.000 description 1
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Abstract
本发明涉及一种合成2‑(1,3,5‑三芳基‑1‑H‑吡唑‑4‑基)丙二腈类化合物的方法,系由方便易得的α‑卤代腙与简单的环丙烯衍生物为原料,在三乙胺促进下,以中等到优秀的收率得到结构多样性的2‑(1,3,5‑三芳基‑1‑H‑吡唑‑4‑基)丙二腈类化合物。本发明方法具有反应条件温和,操作简便、底物适用范围广、区域选择性好等优点。此外,吡唑类化合物骨架具有广谱的生物活性,所得的2‑(1,3,5‑三芳基‑1‑H‑吡唑‑4‑基)丙二腈类化合物在新药研发中具有非常好的应用前景。
Description
技术领域
本发明属于有机化学技术领域,具体涉及一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈系列化合物的制备方法。
背景技术
吡唑是一类含有两个处于相邻位置氮原子的五元芳杂环,其结构有多个可修饰位置(1,3,4,5位),能较容易地进行吡唑类衍生物多样性的合成。吡唑类化合物具有广泛的生物活性,如抗菌、消炎、降血糖、及抗结核等活性。此外,它们也是一类十分重要的杂环农药类化合物,具有良好的除草、杀虫、杀菌等活性。当吡唑环上的3-位或5-位的取代基为芳基时,这类化合物表现出的主要是它的除草活性,例如1993年日本研制开发的吡氟苯草酯,它可以很好地防止小麦田里的诸如小野芝麻、淡甘菊等阔叶杂草;异丙吡草酯经茎叶处理后,敏感植物或杂草迅速吸收,并使植株迅速坏死;Minami,Nobuyoshi报道了几种可以用来作为p38MAPK抑制剂的含吡唑化合物,并研究了它们在治疗炎症、慢性风湿关节炎、哮喘等疾病中的疗效。
吡唑类衍生物因其在医药、农药等领域的广泛应用而受到越来越多的关注。因此不断努力开发基于吡唑骨架的新型结构及其全新的合成方法是非常必要的。目前利用α,β-不饱和醛酮、1,3-二羰基或3-羰基丙腈双官能团化合物与水合肼或者取代肼的缩合反应来构建吡唑环的方法是最常用的。另一种方法是利用重氮烷烃或腈亚胺与烯烃或炔烃的1,3-偶极环加成反应(Fustero,S.;Sánchez-Roselló,M.;Barrio,P.;Simón-Fuentes,A.Chem.Rev.2011,111,6984.)。其中制备3-芳基-4-取代吡唑的方法主要是通过1,3-偶极环加成反应。例如,2008年,N.M.Abunada等人以腙基溴化物与活波亚甲基化合物为原料,进行1,3-环加成反应,得到了产率良好的多取代吡唑(N.M.Abunada,H.M.Hassaneen,N.G.Kandile and O.A.Miqdad,Molecules,2008,13,1501.)。Aggarwal,V.K.等人报道了利用重氮化合物与炔1,3-偶极环加成原位生成吡唑,重氮化合物是利用醛和TsNHNH2产生,然后再和末端炔区域选择性合成3,5-二取代吡唑(Aggarwal,V.K.,Vicente,J.;Bonnert,R.V.A Novel One-Pot Method for the Preparation of Pyrazoles by 1,3-DipolarCycloadditions of Diazo Compounds Generated in Situ.J.Org.chem.,2003,68,5381-5383.)。虽然通过上述方法在合成取代吡唑衍生物上已经取得了一些满意的结果,但是仍然存在底物的局限性(如重氮烷烃有潜在的爆炸性等)及产物的区域选择性的问题。因此不断努力开发基于吡唑骨架的新型结构及其全新的合成方法是非常必要的。
发明内容
本发明的目的在于提供一种由碱促进的全新高效、条件温和的制备方法,能用于制备结构多样的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物。这类化合物是制备药物分子的重要中间体。本发明的这一路线具有反应步骤简单、收率高、成本低和高区域选择性等 优点,便于操作。
本发明的方法进一步描述为在有机溶剂中,使α-卤代腙与1,1-二氰基-2-芳基环丙烯,在碱促进下,反应温度为25-60℃反应,反应5-12小时,后处理得到所述的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物;
所述的α-卤代腙的结构如式(II)所示:
所述的1,1-二氰基-2-芳基环丙烯的结构如(III)所示:
所述的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的结构如式(I)所示:
式(I)-式(III)中,R1为氢、C1-4的烷基、卤素或C1-4烷氧基;
R2为氢、C1-4的烷基、卤素或C1-4烷氧基;
X为氯、溴;
R3为取代的苯基(取代基为叔丁基、甲基、卤素)。
R1的取代位置可以为邻位、对位或者间位。
R2的取代位置可以为邻位、对位或者间位。
反应式如下:
本发明所述的α-卤代腙、1,1-二氰基-2-芳基环丙烯和碱的摩尔比为(1.2-3)∶1∶(2-5)。
本发明所涉及使用的碱优选为三乙胺。
本发明所涉及使用的有机溶剂为1,2-二氯乙烷和甲醇,优选为甲醇。反应浓度范围为0.1mmol/mL-1mmol/mL,优选浓度为0.2mmol/mL-0.4mmo1/mL。
作为优选,所述的反应温度范围为25-35℃。
作为优选,所述的反应时间为5-8小时,反应时间过长增加反应成本,相反则难以使反应原料转化完全。
本发明中,所述的后处理过程包括:洗涤,分液,过滤,硅胶拌样,最后经过柱层析纯化得到相应的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物;或者通过重结晶的手段也可以得到产物。
作为优选R1为氢、甲基、甲氧基、氟、氯、溴。
作为优选R2为氢、甲基、氯、溴。
作为优选X为氯。
作为优选R3为4-叔丁基苯基、3-甲基苯基、3-氯苯基、4-氟苯基。
本发明提供了一种以方便易得的α-卤代腙与简单的环丙烯为原料,在三乙胺促进下,以中等到优秀的收率得到各种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物的方法。本发明方法有反应条件温和,操作简便、底物适用范围广、且区域选择性好等优点,可根据实际需要设计合成不同取代的1-H吡唑类化合物,实用性较强。而且此类化合物骨架具有广谱的生物活性,在医药、农药等领域具有非常好的应用前景。
具体实施方式
下面结合具体实施例对本发明作进一步描述,但并不限制本发明的内容。
按照表1的原料配比在35ml的Schlenk管中加入α-卤代腙、1,1-二氰基-2-芳基环丙烯、三乙胺和有机溶剂2ml,混合搅拌均匀,按照表2的反应条件,TLC监测结束,用水洗涤反应液,用乙酸乙酯萃取,有机层用饱和食盐水洗涤,分液,有机相用无水硫酸钠干燥,过滤,浓缩并柱层析分离得到相应的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物,反应过程如下式所示:
表1
表2
表1和表2中,T为反应温度,t为反应时间,Me为甲基,MeO为甲氧基,Cl为氯基,F为氟基,Br为溴基,t-Bu为叔丁基,Ph为苯基,MeOH为甲醇。
实例1~8制备得到化合物的结构确认数据:
由实施例1制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-1)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.75(d,J=7.8Hz,2H),7.55(t,J=7.6Hz 2H),7.48(d,J=7.5Hz,3H),7.33(d,J=7.3Hz,5H),5.05(s,1H),1.34(s,9H).13C NMR(151MHz,CDCl3)δ153.54(s),151.18(s),143.68(s),139.01(s),129.49(s),129.10(s),128.94(s),128.47(s),126.40(s),124.85(s),111.60(s),34.89(s),31.13(s),19.57(s);HRMS(ESI)calcdfor C28H25N4[M+H]+417.2074,found 417.2079.
由实施例2制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-2)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.64(d,J=7.6Hz,2H),7.48(d,J=7.5Hz,2H),7.36-7.25(m,9H),5.05(s,1H),2.43(s,3H),1.34(s,9H).13C NMR(151MHz, CDCl3)δ153.46(s),151.21(s),143.57(s),139.24(s),129.79(s),129.47(s),128.90(s),128.29(s),127.88(s),126.36(s),124.84(s),124.40(s),111.64(s),34.87(s),31.12(s),21.38(s),19.58(s);HRMS(ESI)calcd for C29H27N4[M+H]+431.2230,found 431.2247.
由实施例3制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-3)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.69(d,J=7.7Hz,2H),7.47(d,J=7.5Hz,2H),7.31(s,4H),7.24(d,J=7.2Hz,2H),7.07(d,J=7.1Hz,2H),5.04(s,1H),3.87(s,3H),1.34(s,9H).13C NMR(151MHz,CDCl3)δ160.39(s),153.45(s),151.00(s),143.51(s),139.05(s),129.75(s),129.45(s),128.91(s),127.87(s),126.37(s),124.82(s),124.42(s),123.22(s),114.52(s),55.31(s),34.87(s),31.12(s),19.61(s).HRMS(ESI)calcd for C29H27N4O[M+H]+447.2179,found 447.2161.
由实施例4制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-4)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.73(d,J=7.7Hz,2H),7.57-7.50(m,5H),7.29-7.25(m,6H),5.03(s,1H),1.36(s,9H).13C NMR(151MHz,CDCl3)δ153.90(s),151.49(s),143.74(s),137.54(s),133.76(s),130.65(s),129.46(s),129.18(d,J=2.7Hz),128.46(s),126.62(s),125.89(s),124.04(s),111.48(s),34.97(s),31.15(s),19.52(s);HRMS(ESI)calcdfor C28H24N4Cl[M+H]+451.1684,found 451.1677.
由实施例5制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-5)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.73(d,J=7.7Hz,2H),7.56-7.50(m,5H),7.45(d,J=7.5Hz,2H),7.21(d,J=7.2Hz,2H),5.03(s,1H),1.36(s,9H).13C NMR(151MHz,CDCl3)δ153.90(s),151.51(s),143.68(s),138.03(s),132.11(s),130.63(s),129.47(s),129.44(s),129.17(s),128.44(s),126.63(s),126.11(s),124.01(s),121.72(s),111.45(s),34.96(s),31.14(s),19.50(s);HRMS(ESI)calcd for C28H24N4Br[M+H]+495.1179,found495.1201.
由实施例6制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-6)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.62(d,J=7.6Hz,2H),7.35(d,J=7.4Hz,3H),7.33-7.28(m,7H),7.19(s,1H),7.11(d,J=7.1Hz,1H),5.05(s,1H),2.44(s,3H),2.37(s,3H).13C NMR(151MHz,CDCl3)δ151.19(s),139.33(s),139.30(s),130.93(s),130.33(s),129.83(s),129.27(s),128.91(s),128.30(s),127.89(s),127.93(s),127.85(s),127.46(s),126.96(s),124.79(s),111.60(s),21.37(s),21.34(s),19.52(s);HRMS(ESI)calcd for C26H21N4[M+H]+389.1761,found 389.1775.
由实施例7制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-7)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)67.59(d,J=7.6Hz,2H),7.48(d,J=7.5Hz,1H),7.43(t,J=7.4Hz,1H),7.37-7.35(m,7H),7.29(dd,J=19.4,7.1Hz,4H),5.06(s,1H),2.45(s,4H),1.57(s,2H).13C NMR(151MHz,CDCl3)δ151.42(s),139.57(s),138.61(s),135.45(s),130.72(s),130.49(s),129.96(s),129.92(s),129.34(s),129.17(s),128.39(s),128.32(s),128.13(s),127.50(s), 124.95(s),111.40(s),21.40(s),19.41(s);HRMS(ESI)calcdfor C25H18N4Cl[M+H]+409.1215,found 409.1233.
由实施例8制备得到的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物(I-8)的核磁共振(1H NMR和13C NMR)和高分辨质谱检测数据为:
1H NMR(600MHz,CDCl3)δ7.58(d,J=7.6Hz,2H),7.38-7.29(m,9H),7.20(t,J=7.2Hz,2H),5.06(s,1H),2.45(s,3H).13C NMR(151MHz,CDCl3)δ164.43(s),162.76(s),151.30(s),142.55(s),139.51(s),138.76(s),132.05(s),132.00(s),129.97(s),129.10(s),128.29(s),128.24(s),127.61(s),124.98(s),123.64(s),123.62(s)116.89(s),116.75(s),111.50(s),21.39(s),19.45(s);HRMS(ESI)calcd for C25H18N4F[M+H]+393.1510,found 393.1518.
Claims (6)
1.一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的制备方法,其特征在于:在有机溶剂中,使α-卤代腙与1,1-二氰基-2-芳基环丙烯,在碱促进下,反应温度为25-35℃反应反应5-8小时,后处理得到所述的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合物;
所述的α-卤代腙的结构如式(II)所示:
所述的1,1-二氰基-2-芳基环丙烯的结构如式(III)所示:
所述的2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈类化合的结构如式(I)所示:
式(I)-式(III)中,R1为氢、C1-4的烷基、卤素或C1-4烷氧基;
R2为氢、C1-4的烷基、卤素或C1-4烷氧基;
X为氯、溴;
R3为取代的苯基(取代基为4-叔丁基-苯基、3-甲基-苯基、3-氯-苯基、4-氟-苯基)。
2.如权利要求1所述的一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的制备方法,其特征在于,所述的卤代腙、1,1-二氰基-2-芳基环丙烯、碱的摩尔比为1.2∶1∶3。
3.如权利要求1所述的一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的制备方法,其特征在于所述的碱为三乙胺。
4.如权利要求1所述的一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的制备方法,其特征在于所述的有机溶剂为甲醇。
5.如权利要求1所述的一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的制备方法,其特征在于所述的反应温度为25-35℃。
6.如权利要求1所述的一种2-(1,3,5-三芳基-1-H-吡唑-4-基)丙二腈的制备方法法,其特征在于反应时间为5-8小时。
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