CN106187961B - 一种2-氨基-5-叠氮基甲基呋喃的制备方法 - Google Patents
一种2-氨基-5-叠氮基甲基呋喃的制备方法 Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- XYAPQAAJPUDYMO-UHFFFAOYSA-N 5-azido-3-methylfuran-2-amine Chemical class NC=1OC(=CC=1C)N=[N+]=[N-] XYAPQAAJPUDYMO-UHFFFAOYSA-N 0.000 title claims description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 7
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- 239000011630 iodine Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- -1 acrylamide compound Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical group 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 4
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000012805 post-processing Methods 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001540 azides Chemical class 0.000 abstract description 3
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- 238000007366 cycloisomerization reaction Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000005610 enamide group Chemical group 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
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- 239000007788 liquid Substances 0.000 description 8
- 238000011017 operating method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 CCCCN(*)C(C(C(*)=C)c(cccc1)c1Cl)=O Chemical compound CCCCN(*)C(C(C(*)=C)c(cccc1)c1Cl)=O 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
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- 229910002027 silica gel Inorganic materials 0.000 description 2
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- 238000004293 19F NMR spectroscopy Methods 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AZYNLUFWNYJNHT-UHFFFAOYSA-N NC1=C(OC(=C1)N=[N+]=[N-])C Chemical class NC1=C(OC(=C1)N=[N+]=[N-])C AZYNLUFWNYJNHT-UHFFFAOYSA-N 0.000 description 1
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/66—Nitrogen atoms
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
一种2‑氨基‑5‑叠氮基甲基呋喃的制备方法，将钯催化剂、TMSN3和高碘试剂溶解在有机溶剂中，加入高联烯酰胺类化合物形成反应体系，反应体系在室温下反应4小时，经后处理得到2‑氨基‑5‑叠氮基甲基呋喃。该方法实现了高联烯酰胺的叠氮化环异构化反应，底物适用范围广，官能团兼容性好，反应在室温下进行，操作简单，具有良好应用前景。
Description
技术领域
本发明属于有机合成领域，具体涉及一种2-氨基-5-叠氮基甲基呋喃的制备方法。
背景技术
2-氨基呋喃及其衍生物具有良好的化学反应活性，可以顺利发生取代、氧化、卤代、Diels-Alder和环加成等众多化学转化，是合成非环、碳环以及杂环化合物的常见中间体，在有机合成、精细化工和材料制备等方面有着广泛应用。
有机叠氮化合物是一类重要的有机合成中间体,是一类重要的有机合成中间体,已广泛应用于有机合成、精细化工、化学生物学、功能材料及临床医药等领域。自2001年由Scripps研究所的Sharpless课题组首次提出“click chemistry”的概念以来，以叠氮化合物与末端炔烃为底物的CuAAC反应合成三氮唑类衍生物成为“点击化学”中的经典，此环加成反应可形成氮杂环并实现多种配体、合成砌块的连接与自组装以及生物分子的偶联；其curtius重排可生成异氰酸酯并转化为胺类化合物,制成固载试剂后可用于多种化学反应；作为一种重要的活性中间体及保护与离去基团,在天然与生理活性化合物和药物合成中也占有重要地位。
2-氨基-5-叠氮基甲基呋喃是一种含高活性官能团叠氮基的2-氨基呋喃类化合物，有着重要的合成和研究意义。
发明内容
本发明要解决的技术问题是提供了一种简单、高效的2-氨基-5-叠氮基甲基呋喃制备方法。
为解决该技术问题本发明采用的技术方案为：
一种2-氨基-5-叠氮基甲基呋喃的制备方法，包括如下步骤：
将钯催化剂、TMSN3和高碘试剂溶解在有机溶剂中，加入结构式Ⅱ所示的高联烯酰胺类化合物形成反应体系，反应体系在室温下反应4小时，经后处理得到结构式Ⅰ所示的2-氨基-5-叠氮基甲基呋喃。
所述的高联烯酰胺化合物结构如式Ⅱ所示：
所述的2-氨基-5-叠氮基甲基呋喃结构如式Ⅰ所示：
式Ⅰ和式Ⅱ中，R为氢原子、甲基、甲氧基、氟原子、氯原子、溴原子或硝基。
所述的钯催化剂为醋酸钯，所述的高碘试剂为PhI(OCCF3)2，所述有机溶剂为乙腈。
所述钯催化剂、TMSN3、高碘试剂、结构式Ⅱ所示化合物的摩尔比为0.05：2：0.7：1。
优选条件的反应路线如下：
所述的反应完全后采用加水淬灭、萃取、有机相经洗涤、干燥和柱层析分离等技术进行后处理，以得到高纯度的产物。
所述的萃取可采用乙酸乙酯作为萃取剂。
所述的洗涤可采用饱和食盐水洗。
所述的柱层析分离的条件为：硅胶300-400目，洗脱液：石油醚/乙酸乙酯的体积比为5/1。
该制备方法，钯催化高联烯酰胺的叠氮化环异构化反应，一锅法高效构建起了2-氨基-5-叠氮基甲基呋喃化合物，反应收率良好，对于合成2-氨基-5-叠氮基甲基呋喃类天然产物或药物具有良好的应用前景。
同现有技术相比，本发明具有如下优点：1、首次实现了高联烯酰胺的叠氮化环异构化反应；2、实现了一系列2-氨基-5-叠氮基甲基呋喃的合成，底物适用范围广，官能团兼容性好，反应在室温下进行，操作简单，具有良好应用前景。
具体实施方式
实施例1
一种2-氨基-5-叠氮基甲基呋喃的制备方法，取一支干燥的反应管，称入醋酸钯(2.8mg,0.0125mmol)、TMSN3(58mg,0.5mmol)、PhI(OCCF3)2(56mg,0.175mmol)，然后加入溶于2mL乙腈的高联烯酰胺1a(80mg,0.25mmol)。反应在室温下搅拌4h后，加10mL水淬灭，用乙酸乙酯(10mL)萃取三次，合并后用饱和食用水洗涤有机相，无水硫酸钠干燥。有机相浓缩后用硅胶(300-400目)柱层析分离(洗脱液：石油醚/乙酸乙酯的体积比为5/1)得到73mg白色固体2a，熔点49–51℃，收率81％。产物核磁分析1H NMR(600MHz,CDCl3):δ7.49–7.31(m,5H),4.30(s,2H),3.42(t,J＝7.2Hz,2H),3.02(s,3H),2.02(s,3H),1.32–1.24(m,2H),1.14–1.06(m,2H),0.69(t,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3):δ142.8,140.9,130.7,129.1,128.4,127.7,124.7,120.2,50.8,45.1,39.7,30.3,19.4,13.4,9.2；HRMS(ESI)calcd forC17H23N4O3S(M+H)+363.1491,found 363.1477。反应式如下：
实施例2
除用结构式1b所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2b所示的化合物，产率：84％，无色液体。1H NMR(600MHz,CDCl3):δ7.34(d,J＝8.0Hz,2H),7.22(d,J＝8.0Hz,2H),4.29(s,2H),3.42(t,J＝7.2Hz,2H),3.01(s,3H),2.37(s,3H),2.01(s,3H),1.32–1.26(m,2H),1.17–1.08(m,2H),0.72(t,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3):δ142.7,140.9,137.5,129.2,129.0,127.8,124.6,120.4,50.8,45.1,39.8,30.3,21.2,19.5,13.4,9.2；HRMS(ESI)calcd forC18H25N4O3S(M+H)+377.1647,found 377.1642.
反应式如下：
实施例3
除用结构式1c所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2c所示的化合物，产率：83％，无色液体；1H NMR(600MHz,CDCl3):δ7.46–7.31(m,2H),6.98–6.92(m,2H),4.29(s,2H),3.83(s,3H),3.42(t,J＝7.2Hz,2H),3.03(s,3H),2.01(s,3H),1.31–1.26(m,2H),1.16–1.07(m,2H),0.72(t,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3):δ159.1,142.7,140.7,130.3,124.4,123.0,120.3,113.9,55.2,50.7,45.1,39.7,30.3,19.5,13.4,9.2；HRMS(ESI)calcd forC18H25N4O4S(M+H)+393.1597,found 393.1595.
反应式如下：
实施例4
除用结构式1d所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2d所示的化合物，产率：77％，无色液体；1H NMR(600MHz,CDCl3):δ7.34–7.28(m,1H),7.16–7.08(m,1H),7.06–6.97(m,1H),6.94–6.84(m,1H),4.30(s,2H),3.83(s,3H),3.42(t,J＝7.2Hz,2H),3.04(s,3H),2.03(s,3H),1.32–1.25(m,2H),1.15–1.07(m,2H),0.71(t,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3):δ159.5,142.9,141.0,132.0,129.3,124.7,121.3,120.2,114.3,113.9,55.3,50.8,45.1,39.8,30.3,19.5,13.4,9.2；HRMS(ESI)calcd for C18H25N4O4S(M+H)+393.1597,found393.1594.
反应式如下：
实施例5
除用结构式1e所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2e所示的化合物，产率：70％，无色液体；1H NMR(400MHz,CDCl3):δ7.55(d,J＝8.3Hz,2H),7.36(d,J＝8.3Hz,2H),4.30(s,2H),3.42(t,J＝7.2Hz,2H),3.07(s,3H),2.00(s,3H),1.29–1.22(m,2H),1.16–1.05(m,2H),0.72(t,J＝7.3Hz,3H)；13C NMR(100MHz,CDCl3):δ143.1,141.0,131.7,130.8,129.7,123.9,122.1,120.0,50.7,45.1,39.7,30.2,19.5,13.4,9.2；HRMS(ESI)calcd for C17H22BrN4O3S(M+H)+441.0596,found 441.0611.
反应式如下：
实施例6
除用结构式1f所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2f所示的化合物，产率：79％，无色液体；1H NMR(400MHz,CDCl3):δ7.49–7.35(m,4H),4.30(s,2H),3.42(t,J＝7.2Hz,2H),3.07(s,3H),2.01(s,3H),1.29–1.21(m,2H),1.16–1.05(m,2H),0.72(t,J＝7.3Hz,3H)；13C NMR(100MHz,CDCl3):δ143.1,141.1,133.9,130.5,129.2,128.7,123.9,120.1,50.7,45.1,39.7,30.3,19.5,13.4,9.2；HRMS(ESI)calcd for C17H22ClN4O3S(M+H)+397.1101,found397.1105.
反应式如下：
实施例7
除用结构式1g所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2g所示的化合物，产率：73％，无色液体；1H NMR(600MHz,CDCl3):δ7.61–7.53(m,1H),7.47–7.42(m,1H),7.36–7.31(m,2H),4.40–4.21(m,2H),3.45–3.37(m,2H),3.05(s,3H),1.91(s,3H),1.39–1.32(m,2H),1.15–1.03(m,2H),0.75(t,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3):δ142.5,141.3,134.0,132.8,129.9,129.7,129.2,127.0,123.2,121.9,50.7,45.1,39.7,30.1,19.4,13.4,9.0；HRMS(ESI)calcd for C17H22ClN4O3S(M+H)+397.1101,found 397.1101.
反应式如下：
实施例8
除用结构式1h所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2h所示的化合物，产率：72％，无色液体；1H NMR(600MHz,CDCl3):δ7.51–7.41(m,2H),7.16–7.04(m,2H),4.30(s,2H),3.42(t,J＝7.2Hz,2H),3.07(s,3H),2.00(s,3H),1.27–1.23(m,2H),1.13–1.05(m,2H),0.71(t,J＝7.4Hz,3H)；13C NMR(151MHz,CDCl3):δ162.4(d,J＝247.3Hz),143.0,141.0,130.9(d,J＝8.1Hz),126.7(d,J＝3.3Hz),124.1,120.2,115.5(d,J＝21.5Hz),50.7,45.1,39.6,30.2,19.5,13.4,9.2；19F NMR(565MHz,CDCl3)δ–114.1；HRMS(ESI)calcd for C17H22FN4O3S(M+H)+381.1379,found 381.1389.
反应式如下：
实施例9
除用结构式1i所示的高联烯酰胺化合物代替实施事例1中结构式1a所示的高联烯酰胺外，其余操作步骤同实施例1，最终得到结构式2i所示的化合物，产率：57％，无色液体；1H NMR(400MHz,CDCl3):δ8.29(d,J＝8.8Hz,2H),7.70(d,J＝8.8Hz,2H),4.33(s,2H),3.44(t,J＝7.2Hz,2H),3.11(s,3H),2.05(s,3H),1.28–1.22(m,2H),1.15–1.04(m,2H),0.70(t,J＝7.3Hz,3H)；13C NMR(100MHz,CDCl3):δ147.3,143.8,141.8,137.7,130.0,123.7,123.3,119.7,50.7,45.0,39.5,30.2,19.5,13.4,9.3；HRMS(ESI)calcd for C17H22N5O5S(M+H)+408.1342,found 408.1341.
反应式如下：
Claims (1)
1.一种2-氨基-5-叠氮基甲基呋喃的制备方法，其特征在于包括如下步骤：
将钯催化剂、TMSN3和高碘试剂溶解在有机溶剂中，加入结构式Ⅱ所示的高联烯酰胺类化合物形成反应体系，反应体系在室温下反应4小时，经后处理得到结构式Ⅰ所示的2-氨基-5-叠氮基甲基呋喃；
式Ⅰ和式Ⅱ中，R为氢原子、甲基、甲氧基、氟原子、氯原子、溴原子或硝基；所述的钯催化剂、TMSN3、高碘试剂、结构式Ⅱ所示的化合物的摩尔比为0.05：2：0.7：1；所述的钯催化剂为醋酸钯，所述的高碘试剂为PhI(OCOCF3)2，所述有机溶剂为乙腈；所述的后处理包括淬灭、萃取、干燥和柱层析。
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