CN117143018A - 一种稀土催化含氮杂环化合物的合成方法 - Google Patents
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- -1 nitrogen-containing heterocyclic compound Chemical class 0.000 title claims abstract description 21
- 229910052761 rare earth metal Inorganic materials 0.000 title claims abstract description 12
- 150000002910 rare earth metals Chemical class 0.000 title claims abstract description 12
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 11
- 238000001308 synthesis method Methods 0.000 title description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 27
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 claims abstract description 15
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 claims abstract description 9
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- 229910052727 yttrium Inorganic materials 0.000 claims description 9
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- 238000006243 chemical reaction Methods 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RXBYRTSOWREATF-UHFFFAOYSA-N 1,2,3,4-tetrahydroacridine Chemical compound C1=CC=C2C=C(CCCC3)C3=NC2=C1 RXBYRTSOWREATF-UHFFFAOYSA-N 0.000 abstract description 15
- 238000002360 preparation method Methods 0.000 abstract description 8
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- 150000001251 acridines Chemical class 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
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- MAVXZXSEKRXRBC-UHFFFAOYSA-N 2-phenyl-1,2,3,4-tetrahydroacridine Chemical compound C1CC2=NC3=CC=CC=C3C=C2CC1C1=CC=CC=C1 MAVXZXSEKRXRBC-UHFFFAOYSA-N 0.000 description 1
- PIXOMBPMAWPFKV-UHFFFAOYSA-N 2-phenylacridine Chemical compound C1=CC=CC=C1C1=CC=C(N=C2C(C=CC=C2)=C2)C2=C1 PIXOMBPMAWPFKV-UHFFFAOYSA-N 0.000 description 1
- BASZRPQRVXBLEA-UHFFFAOYSA-N 5-methyl-1,2,3,4-tetrahydroquinoxaline Chemical compound N1CCNC2=C1C=CC=C2C BASZRPQRVXBLEA-UHFFFAOYSA-N 0.000 description 1
- 239000001640 5-methylquinoxaline Substances 0.000 description 1
- SBWVMNMIHNOTET-UHFFFAOYSA-N 6-chloro-1,2,3,4-tetrahydroquinoxaline Chemical compound N1CCNC2=CC(Cl)=CC=C21 SBWVMNMIHNOTET-UHFFFAOYSA-N 0.000 description 1
- HOOMNCITVCXDTR-UHFFFAOYSA-N 6-chloroquinoxaline Chemical compound N1=CC=NC2=CC(Cl)=CC=C21 HOOMNCITVCXDTR-UHFFFAOYSA-N 0.000 description 1
- XXGSVEBKGLOFCT-UHFFFAOYSA-N C[Si](C)(C)[Y](N)[Si](C)(C)C Chemical compound C[Si](C)(C)[Y](N)[Si](C)(C)C XXGSVEBKGLOFCT-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
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- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/36—Yttrium
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Abstract
本发明公开了一种稀土催化含氮杂环化合物的合成方法，本发明甲苯为溶剂，对三氟甲基苯胺为添加剂，频哪醇硼烷为氢源，在氮气氛围下，以双三甲基硅氨基钇与三（五氟苯基）硼烷为催化剂，共催化吖啶/喹喔啉类化合物发生氢转移还原反应，从而实现结构多样化的四氢吖啶/四氢喹喔啉的制备，本发明具有原料来源广泛，催化剂简单易制得，操作简便，选择性高，收率高，且反应条件温和，普适性广等优点。
Description
技术领域
本发明属于有机合成技术领域，具体是一种稀土催化含氮杂环化合物的合成方法。
背景技术
四氢吖啶/四氢喹喔啉类化合物是天然存在的生物碱和许多生物活性化合物中普在的结构基序，也是药物合成、农化合成和材料科学的重要组成部分。金属催化的吖啶/喹喔啉苯并噻唑与氢分子的催化加氢反应是制备四氢吖啶/四氢喹喔啉的常见方法。也可以通过催化氢转移还原来制备四氢吖啶/四氢喹喔啉(Chem.Commun.2017,53,9269)。但是，这些反应存在催化剂制备繁琐、反应条件苛刻、底物范围窄、功能相容性低、化学选择性差和产生大量有毒废物等缺点，具有一定的局限性。
发明内容
本发明的目的在于克服现有技术的不足，提供一种稀土催化含氮杂环化合物的合成方法，本发明原料来源广泛、催化剂简单易制得，操作简便，选择性高，收率高，反应条件温和。
本发明的目的是通过以下技术方案来实现的：一种稀土催化含氮杂环化合物的合成方法，以双三甲基硅氨基钇与三(五氟苯基)硼烷为催化剂催化吖啶或喹喔啉，得到对应的含氮杂环化合物。
作为可实施例的一种，所述双三甲基硅氨基钇与三(五氟苯基)硼烷的摩尔比为1：1。
作为可实施例的一种，反应以三氟甲基苯胺为添加剂，甲苯为溶剂，频哪醇硼烷为氢源。
作为可实施例的一种，所述吖啶或喹喔啉、双三甲基硅氨基钇、三(五氟苯基)硼烷、对三氟甲基苯胺和频哪醇硼烷的摩尔比为1：0.1：0.1：0.1：5.0。
一种稀土催化含氮杂环化合物的合成反应式为：
作为可实施例的一种，R为氢或邻位的苯基、甲基和氯的任意一种。
本发明的有益效果是：在双三甲基硅氨基钇/三(五氟苯基)硼烷催化体系下，吖啶/喹喔啉化合物发生氢转移还原反应，从而实现结构多样化的四氢吖啶/四氢喹喔啉的合成。
(1)本发明原料来源广泛，操作简便，普适性广，选择性高，同时环保性和底物普适性有明显改善；
(2)本发明的四氢吖啶/四氢喹喔啉类化合物产率高，反应产率在90％以上，且品质高，后处理方便；
(3)本发明是对四氢吖啶/四氢喹喔啉类化合物制备的重要补充，为生物活性化合物的合成提供了重要思路。
附图说明
图1为实施例1的核磁共振氢谱；
图2为实施例1的核磁共振炭谱；
图3为实施例2的核磁共振氢谱；
图4为实施例2的核磁共振炭谱；
图5为实施例3的核磁共振氢谱；
图6为实施例3的核磁共振炭谱；
图7为实施例4的核磁共振氢谱；
图8为实施例4的核磁共振炭谱；
图9为实施例5的核磁共振氢谱；
图10为实施例5的核磁共振炭谱；
图11为实施例6的核磁共振氢谱；
图12为实施例6的核磁共振炭谱。
具体实施方式
下面结合附图进一步详细描述本发明的技术方案，但本发明的保护范围不局限于以下所述。
实施例1
四氢吖啶的制备，结构式如下：
具体方法包括以下步骤：
将0.5mmol吖啶、0.05mmol双三甲基硅氨基钇、0.05mmol三(五氟苯基)硼烷、0.05mmol对三氟甲基苯胺、2.5mmol频哪醇硼烷、1.5mL甲苯在50℃下反应12小时。
产物分离收率93％，对产物进行检测检测结果如图1-图2。
1H NMR(400MHz,DMSO)δ8.64(s,1H),7.09-6.99(m,4H),6.81-6.72(m,4H),3.95(s,2H)；13C NMR(101MHz,DMSO)δ141.2,128.8,127.3,120.1,119.5,113.8,31.2。
实施例2
2-苯基四氢吖啶的制备，结构式如下：
具体方法包括以下步骤：
将0.5mmol 2-苯基吖啶、0.05mmol双三甲基硅氨基钇、0.05mmol三(五氟苯基)硼烷、0.05mmol对三氟甲基苯胺、2.5mmol频哪醇硼烷、1.5mL甲苯在50℃下反应12小时。
产物分离收率96％，对产物进行检测检测结果如图3-图4。
1H NMR(400MHz,DMSO)δ8.97(s,1H),7.25-7.14(m,4H),7.13-7.05(m,5H),6.94(d,J＝7.7Hz,2H),6.82-6.70(m,2H),5.32(s,1H)；13C NMR(101MHz,DMSO)δ148.7,140.0,129.7,128.9,127.62,127.61,126.5,123.3,120.4,114.4,47.1.
实施例3
四氢喹喔啉的制备，结构式如下：
具体方法包括以下步骤：
将0.5mmol喹喔啉、0.05mmol equiv双三甲基硅氨基钇、0.05mmol equiv三(五氟苯基)硼烷、0.05mmol对三氟甲基苯胺、2.5mmol频哪醇硼烷、1.5mL甲苯在50℃下反应12小时。
产物分离收率95％，对产物进行检测检测结果如图5-图6。
1H NMR(400MHz,CDCl3)δ6.55(s,2H),6.48(s,2H),3.39(s,4H)；13C NMR(101MHz,CDCl3)δ133.8,118.9,114.8,41.5.
实施例4
2-甲基四氢喹喔啉的制备，结构式如下：
具体方法包括以下步骤：
将0.5mmol 2-甲基喹喔啉、0.05mmol双三甲基硅氨基钇、0.05mmol三(五氟苯基)硼烷、0.05mmol对三氟甲基苯胺、2.5mmol频哪醇硼烷、1.5mL甲苯在50℃下反应12小时。
产物分离收率88％，对产物进行检测检测结果如图7-图8。
1H NMR(400MHz,CDCl3)δ6.70(dd,J＝5.4,3.7Hz,2H),6.60(dd,J＝5.2,2.6Hz,2H),3.74-3.48(m,3H),3.40(dd,J＝10.7,2.7Hz,1H),3.13(t,J＝9.4Hz,1H),1.32-1.23(m,3H)；13C NMR(101MHz,CDCl3)δ133.6,133.2,118.6,114.48,114.42,48.2,45.7,19.9.
实施例5
5-甲基四氢喹喔啉的制备，结构式如下：
具体方法包括以下步骤：
将0.5mmol 5-甲基喹喔啉、0.05mmol双三甲基硅氨基钇、0.05mmol三(五氟苯基)硼烷、0.05mmol对三氟甲基苯胺、2.5mmol频哪醇硼烷、1.5mL甲苯在50℃下反应12小时。
产物分离收率91％，对产物进行检测检测结果如图9-图10。
1H NMR(400MHz,CDCl3)δ6.65-6.51(m,2H),6.43(dd,J＝6.7,2.6Hz,1H),3.63-3.47(m,4H),3.46-3.39(m,2H),2.12(s,3H).13C NMR(101MHz,CDCl3)δ133.2,131.7,122.2,120.4,118.0,112.9,41.8,41.2,17.0.
实施例6
6-氯四氢喹喔啉的制备，结构式如下：
具体方法包括以下步骤：
将0.5mmol 6-氯喹喔啉、0.05mmol双三甲基硅氨基钇、0.05mmol三(五氟苯基)硼烷、0.05mmol对三氟甲基苯胺、2.5mmol频哪醇硼烷、1.5mL甲苯在50℃下反应12小时。
产物分离收率92％，对产物进行检测检测结果如图11-图12。
1H NMR(400MHz,CDCl3)δ6.51(dd,J＝8.3,2.3Hz,1H),6.44(d,J＝2.3Hz,1H),6.38(d,J＝8.2Hz,1H),3.58(s,2H),3.38(s,4H).13C NMR(150MHz,CDCl3)δ134.8,132.0,123.3,118.0,115.4,114.0,4.
对比例1
在实施例1的基础上，仅以双三甲基硅氨基钇为催化剂，产率为71％。
对比例2
在实施例1的基础上，仅以三(五氟苯基)硼烷为催化剂，产率为66％。
以上所述仅是本发明的优选实施方式，应当理解本发明并非局限于本文所披露的形式，不应看作是对其他实施例的排除，而可用于各种其他组合、修改和环境，并能够在本文所述构想范围内，通过上述教导或相关领域的技术或知识进行改动。而本领域人员所进行的改动和变化不脱离本发明的精神和范围，则都应在本发明所附权利要求的保护范围内。
Claims (6)
1.一种稀土催化含氮杂环化合物的合成方法，其特征在于：以双三甲基硅氨基钇与三（五氟苯基）硼烷为催化剂催化吖啶或喹喔啉，得到对应的含氮杂环化合物。
2.根据权利要求1所述的一种稀土催化含氮杂环化合物的合成方法，其特征在于：所述双三甲基硅氨基钇与三（五氟苯基）硼烷的摩尔比为1：1。
3.根据权利要求1所述的一种稀土催化含氮杂环化合物的合成方法，其特征在于：反应以三氟甲基苯胺为添加剂，甲苯为溶剂，频哪醇硼烷为氢源。
4.根据权利要求3所述的一种稀土催化含氮杂环化合物的合成方法，其特征在于：所述吖啶或喹喔啉、双三甲基硅氨基钇、三（五氟苯基）硼烷、对三氟甲基苯胺和频哪醇硼烷的摩尔比为1：0.1： 0.1：0.1：5.0。
5.根据权利要求1-4任一项所述的一种稀土催化含氮杂环化合物的合成方法，其特征在于：反应式为：
。
6.根据权利要求5所述的一种稀土催化含氮杂环化合物的合成方法，其特征在于：R为氢或邻位的苯基、甲基和氯的任意一种。
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