CN109232529B - 一种Rh(III)催化具有氮杂环骨架的化合物的制备方法 - Google Patents
一种Rh(III)催化具有氮杂环骨架的化合物的制备方法 Download PDFInfo
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明公开了一种自组装导向基团辅助Rh(III)催化构建氮杂环骨架的制备方法,包括如下步骤:在铑催化剂和醋酸盐存在的条件下,芳香醛与2‑氨基吡啶在溶剂中发生反应,原位产生一个有效的导向基团。该导向基团再在铑催化下与取代烯烃反应,反应完成后,经过后处理得到所述的氮杂环骨架的化合物。该制备方法使用铑进行催化,成功实现了自组装高效导向基的合成策略。反应从更简单的原料出发,在简洁温和的催化体系中,利用“一锅法”合成了新型取代特征的异吲哚酮骨架和异喹啉结构,操作简便,反应条件温和,收率高,原子经济性高。
Description
技术领域
本发明属于有机合成领域,具体涉及一种自组装导向基团辅助Rh(III)催化构建氮杂环骨架的制备方法。
背景技术
异吲哚酮(γ-内酰胺)是一个较多见而又重要的母核。因α位是具有较强络合力的N原子,故利用苯甲酰胺中的氮原子作为导向原子,并且参与形成γ-内酰胺的研究已多有报道。
李兴伟课题组最早在2010年尝试使用N-苯基取代的芳甲酰胺作为底物,与丙烯酸酯反应构建起异吲哚酮骨架(Org.Lett.,2010,12,5430)。反应中首先生成了Heck产品中间体,进而发生迈克尔加成而环化。但底物中芳环若是呋喃、吲哚等杂环时不利于形成异吲哚酮产品,多是停留在了氧化Heck反应产品上,且反应条件较为苛刻。反应式如下:
2014年,于金权课题组对以上反应进行了改良。他们使用了N-全氟取代苯基芳甲酰胺作为底物(Chem.Sci.,2015,6,1923),实际上就是增大酰胺中氮原子上取代基的拉电子能力,减弱酰胺键的异构化而增加其亲核性。这一工作虽然扩宽了底物类别,对于杂环如噻吩、呋喃、吡啶都有很好的适用性,且反应条件变得较为温和,但其底物的普适性仍不够广泛,且原料较为复杂,制备过程不够简单。
发明内容
本发明提供了一种自组装导向基团辅助Rh(III)催化构建氮杂环骨架的方法,该制备方法能够原位产生一个有效的新型导向基团,并且原料简单,反应条件温和,反应收率高,原子经济性高。
一种自组装导向基团辅助Rh(III)催化构建氮杂环骨架的制备方法,包括如下步骤:在铑催化剂和醋酸盐存在的条件下,芳香醛与2-氨基吡啶在溶剂中发生反应,原位产生一个有效的导向基团。该导向基团再在铑催化下与取代烯烃反应,反应完成后,经过后处理得到所述的氮杂环骨架的化合物。
所述的芳香醛的结构如式(Ⅰ)所示:
所述的2-氨基吡啶的结构如式(Ⅱ)所示:
所述的取代烯烃的结构如式(Ⅲ)所示:
所述的氮杂环骨架的化合物的结构如式(IV)所示:
式(Ⅰ)~式(IV)中,R为烷基、烷氧基、氢原子、卤素原子、氰基、酯基、硝基、三氟甲基;
R’为烷氧酰基、烷酰基、氰基、酰胺。
所述的反应反应式如下:
推测该反应机理为:
首先,芳香醛与2-氨基吡啶发生缩合反应,在原位产生一个有效的新型导向基团。如下所示:
接着,自组装导向基与取代烯烃在金属铑(III)催化下发生如下反应:
作为优选,所述的铑催化剂为[Cp*RhCl2]2(CAS:12354-85-7),用量为2mol%,该种铑催化剂对本发明中的底物的催化效率高。
作为优选,所述的醋酸盐为醋酸铜,用量为2eq。该醋酸盐起到氧化剂的作用,有助于铑催化剂在反应中的催化。
作为优选,以摩尔量计,芳香醛、2-氨基吡啶和取代烯烃用量比为1:1.2~2:1.2~2。
作为优选,所述的R为C1~C5烷基、C1~C5烷氧基、氢原子、卤素原子、氰基、酯基、硝基、三氟甲基,这些取代基均可以使反应顺利进行。
作为优选,所述的R’为C1~C5烷氧酰基、C1~C5烷酰基、氰基、酰胺,这些取代基均为吸电子取代基,有利于提高所述的取代烯烃的反应活性,有助于Michael加成反应的进行。
作为优选,所述的溶剂为乙腈、水、甲醇、乙醇、DMF、DMSO和THF中的至少一种,这些溶剂都为极性溶剂,有利于底物中C-H键的断裂,作为进一步的优选,所述的溶剂为乙腈。
作为优选,反应的温度为80~110℃,反应温度过高,会使得副反应增多,反应温度过低,会降低反应物的转化率,作为进一步的优选,反应的温度为80℃。
作为优选,反应的氛围为空气、氮气中的一种,在这些氛围中,均能使反应更好进行,具有较高产率,作为进一步的优选,反应的氛围为N2氛围。
本发明中,反应的时间可以通过TLC进行监测,在80℃下搅拌4~12小时反应能够发生完全。
为了提高反应的收率,可以先将芳香醛类化合物、2-氨基吡啶、Cu(OAc)2和[Cp*RhCl2]2加入Schlenk瓶中,然后对其进行抽真空处理再通入氮气,操作三次后,再加入溶剂和取代烯烃。
同现有技术相比,本发明的有益效果体现在:该反应采用“一锅法”制备,操作简单。反应中可自生成高效导向基团。合成的新型取代特征的异吲哚酮骨架和异喹啉结构产物收率高,反应所需的原料简单易得,反应原子经济性高,催化体系简洁温和,符合绿色化学的要求。
附图说明
图1为实施例1制得的产物的1HNMR谱图;
图2为实施例1制得的产物的13CNMR谱图;
图3为实施例2制得的产物的1HNMR谱图;
图4为实施例2制得的产物的13CNMR谱图。
具体实施方式
实施例1
在25mL的Schlenk瓶中,称入24mg(0.2mmol)对甲基苯甲醛(1.5eq),Cu(OAc)253mg(2.0eq),2-氨基吡啶25mg(2.0eq),[Cp*RhCl2]2 3mg(2%)。然后对其进行抽真空处理再通入氮气,操作三次后,加入2mL乙腈,搅拌10min,再加入丙烯酸乙酯45μL(2.0eq),在80℃下氮气氛围中恒温搅拌。约5h后TLC检测反应完毕,加入些许硅胶,蒸出溶剂,固化,固体上样,进行柱色谱分离。得产品55mg,收率90%。反应式如下:
产品物理性质及谱图数据如下:白色固体;熔点:90-92℃;1H NMR(CDCl3,600MHz)δ8.54(d,J=12.6Hz,1H),8.42-8.40(m,1H),7.81-7.73(m,2H),7.39(s,1H),7.31(d,J=12Hz,1H),7.07-7.04(m,1H),5.95-5.92(m,1H),4.12-4.08(m,2H),3.33(dd,J1=24Hz,J2=5.4Hz),2.81-2.75(m,1H),2.47(s,3H),1.16(t,J=10.8Hz,3H)ppm;13C NMR(CDCl3,150MHz)δ170.7,167.7,151.1,147.7,145.4,143.8,138.0,129.8,129.4,124.1,123.3,119.4,115.7,60.7,56.4,38.2,22.2,14.2ppm.
实施例2
在25mL的Schlenk瓶中,称入21mg(0.2mmol)苯甲醛(1.0eq),Cu(OAc)2 80mg(2.0eq),2-氨基吡啶38mg(2.0eq),[Cp*RhCl2]2 4.96mg(2%)。然后对其进行抽真空处理再通入氮气,操作三次后,加入2mL乙腈,搅拌10min,再加入丙烯酸乙酯43mL(2.0eq),在80℃下氮气氛围中恒温搅拌。约5h后TLC检测反应完毕,加入些许硅胶,蒸出溶剂,固化,固体上样,进行柱色谱分离。得产品51mg,收率85%。反应式如下:
产品物理性质及谱图数据如下:白色固体;熔点:123-125℃;1H NMR(CDCl3,600MHz)δ8.54(d,J=11.4Hz,1H),8.42(m,1H),7.92(d,J=11.4Hz,1H),7.79-7.74(m,1H),7.60(m,2H),7.53-7.49(m,1H),7.09-7.06(m,1H),5.98(m,1H),4.11-4.05(m,2H),3.35(dd,J1=24Hz,J2=5.4Hz,1H),2.78(m,1H),1.15(t,J=10.8Hz,3H)ppm;13C NMR(CDCl3,150MHz)δ170.7,167.7,151.0,147.9,145.0,138.1,133.0,132.0,128.8,124.4,123.0,119.7,115.9,60.8,56.6,38.2,14.2ppm.。
Claims (6)
1.一种Rh(III)催化具有氮杂环骨架的化合物的制备方法,其特征在于,包括如下步骤:在铑催化剂和醋酸盐存在的条件下,芳香醛与2-氨基吡啶在溶剂中发生反应,原位生成含导向基团的中间体;该中间体再在铑催化下与取代烯烃反应,反应完成后,经过后处理得到所述的氮杂环骨架的化合物;
所述的芳香醛的结构如式(Ⅰ)所示:
所述的2-氨基吡啶的结构如式(Ⅱ)所示:
所述的取代烯烃的结构如式(Ⅲ)所示:
所述的具有氮杂环骨架的化合物的结构如式(IV)所示:
式(Ⅰ)~式(IV)中,R为C1~C5烷基、C1~C5烷氧基、氢原子、卤素原子、氰基、硝基、三氟甲基;
R’为C1~C5烷氧酰基、C1~C5烷酰基或氰基;
所述的铑催化剂为[Cp*RhCl2]2;
所述的醋酸盐为醋酸铜。
2.根据权利要求1所述的Rh(III)催化具有氮杂环骨架的化合物的制备方法,其特征在于,所述的铑催化剂用量为芳香醛的2mol%。
3.根据权利要求1或2所述的Rh(III)催化具有氮杂环骨架的化合物的制备方法,其特征在于,所述的醋酸盐用量为芳香醛摩尔量的1.2~2.0倍。
4.根据权利要求1所述的Rh(III)催化具有氮杂环骨架的化合物的制备方法,其特征在于,所述的溶剂为乙腈、水、甲醇、乙醇、DMF、DMSO和THF中的至少一种。
5.根据权利要求1所述的Rh(III)催化具有氮杂环骨架的化合物的制备方法,其特征在于,反应的温度为60~110℃。
6.根据权利要求1所述的Rh(III)催化具有氮杂环骨架的化合物的制备方法,其特征在于,反应的氛围为空气、氮气中的一种。
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