CN106946862A - 1‑烷烃‑6‑甲基‑5‑硝基‑1h‑苯并[d]咪唑类化合物及其制备方法 - Google Patents
1‑烷烃‑6‑甲基‑5‑硝基‑1h‑苯并[d]咪唑类化合物及其制备方法 Download PDFInfo
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 26
- -1 glyoxaline compound Chemical class 0.000 title claims abstract description 20
- 229940049706 benzodiazepine Drugs 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 title abstract 4
- 150000001335 aliphatic alkanes Chemical class 0.000 title abstract 3
- 125000005605 benzo group Chemical group 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000000376 reactant Substances 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 229940126214 compound 3 Drugs 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 abstract 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 150000004941 2-phenylimidazoles Chemical class 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000005612 Grewia tenax Nutrition 0.000 description 1
- 244000041633 Grewia tenax Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 240000005308 Juniperus chinensis Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
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- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000004841 phenylimidazoles Chemical class 0.000 description 1
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- 239000004575 stone Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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Abstract
本发明公开了1‑烷烃‑6‑甲基‑5‑硝基‑1H‑苯并[D]咪唑类化合物及其制备方法，在微波反应器中，加入(E1)‑N’(2‑氟‑4‑甲基5‑硝基‑苯)‑N,N‑二甲基‑甲脒，干燥的溶剂及相应的胺，反应混合物在110‑180℃下与微波炉加热10‑30min,反应产物经过反相色谱纯化后得到目标产物化合物。本发明制备方法简单，与传统方法相比表现出极高的选择性，原料易得，所得化合物结构中苯并咪唑基团本身具有良好的药物活性，经过本发明修饰后的结构，形成了1‑烷烃‑6‑甲基‑5‑硝基‑1H‑苯并[D]咪唑类化合物，其中的硝基可以被还原成氨基，由此可以合成许多衍生物，可为其在生物活性方面的研究提供技术支持。
Description
技术领域
本发明涉及1位取代的新型的苯并咪唑化合物，具体为1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物及其制备方法。
背景技术
几十年来，苯并咪唑及其衍生物的合成及应用研究是精细有机合成的研究热点。苯并咪唑类化合物是一种含有两个氮原子的苯并杂环化合物,苯并咪唑及其衍生物在抗癌、抗真菌、镇痛消炎、抗风湿、驱虫等方面有很重要的药用价值。苯并咪唑类化合物还是一种针对碳钢在酸性环境中腐蚀的优良缓蚀剂。
孙磉礅等在物理化学学报(Wuli Huaxue Xuebao)Acta Phys.-Chim.Sin.2013,29(6),1192-1200)中,采用HQSAR方法，对苯并咪唑类缓蚀剂的分子结构与缓蚀性能的定量关系进行研究,设计出了一系列具有较好缓蚀性能的新型苯并咪唑类衍生物。
苏国强、郭涤亮、刘宇、朱兰、边军、朱崇亮报道了2-烷氧基苯并咪唑类化合物的制备方法(CN1425654A)。李焱、马会强、王玉炉报道了一系列苯并咪唑及衍生物(有机化学，2008年第2期,210～217)。韩波，蒋海金，贾小维等报道了以活性炭负载磷酸为催化剂，催化邻苯二胺与苯甲醛合成了1-苄基-2-苯基苯并咪唑(应用化工，2011，40(9)：1553—1555，Gadekar等(Chin.Chem.Lett，2010，21：1053-1056)、Ahmad等(Res.J.Chem.Environ，2013，17(3)：40—45)、Chari等(Tetrahedron Lett，2010，51：5195-5199)分别合成了2-取代苯并咪唑类化合物。
曾庆乐等报道了2-芳基苯并咪唑的合成方法(CN 103755642 A)。涩谷直应岩田效志、木户智史公开了苯基咪唑化合物(CN 102307861 A)。U·克拉尔等公开了一类具有取代基的苯并咪唑化合物。郝新奇等公开了3-(2-硝基-1-苯乙基)-2-(2-苯基咪唑并[1,2-α]吡啶)类化合物(CN 105085520 A)。陈桧华、林伟忠利用邻苯二胺与二分子醛缩合形成分子内双席佛碱，通过发生分子内重排合成了1-取代-2-芳基苯并咪唑衍生物。
苯并咪唑类化合物不仅具有杀菌、抗肿瘤、驱虫等生物活性，而且由于其结构中存在强吸电子基硝基，使得其易于亲电或亲核试剂发生加成反应而成为应用广泛的有机合成中间体。
综上所述，研究开发结构新颖、性能高效的苯并咪唑类化合物具有重要的现实意义和科学价值。在已公开的苯并咪唑类化合物文献资料中均没有1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物。
发明内容
本发明的目的在于提供1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物及其制备方法，以解决上述技术问题。
为实现上述目的，本发明采用的技术方案是:
1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物，其化合物的通式为：
其中：R为
本发明还提供了上述1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物的制备方法，包括下述步骤:利用微波反应，采用以下反应合成得到以下通式中产物化合物3；
具体步骤为在微波反应器中，向微波反应管中加入0.4-0.8mmol化合物1(E1)-N’(2-氟-4-甲基5-硝基-苯)-N,N-二甲基-甲脒，2ml干燥的溶剂，3.0-5.0mmol胺2，反应混合物在微波反应器中110-180℃加热10-30min；用反相高效液相色谱法直接对反应混合物进行纯化,得到产物3。
作为本案发明进一步的方案，所述溶剂为二甘醇、DMSO、DMF、1，2-丙二醇、乙二醇、苄醇、环丁砜的任一种。
本发明的有益效果是：通过本发明制备方法所得化合物结构中苯并咪唑基团本身具有良好的药物活性，经过本发明修饰后的结构，形成了1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物；其中的硝基可以被还原成氨基，由此可以合成许多衍生物，可为其在生物活性方面的研究提供技术支持。
具体实施方式
下面结合具体实施例对本发明作进一步阐述。
实施例1
在微波反应器中，向微波反应管中加入化合物1(0.8mmol)(E1)-N’(2-氟-4-甲基5-硝基-苯)-N,N-二甲基-甲脒【(E)-N'-(2-fluoro-4-methyl-5-nitrophenyl)-N,N-dimethylformamidine)】，干燥的DMSO(2ml)，胺2c(4.0mmol)，反应混合物在微波反应器中180℃加热10min。用反相高效液相色谱法直接对反应混合物进行纯化,得到产物3c。产率为80％。
1H NMR(400MHz,MeOD)ppm 1.55-1.71(m,1H),1.73-1.97(m,2H),2.06-2.19(m,1H),2.69(s,3H),3.69-3.79(m,1H),3.79-3.89(m,1H),4.20-4.34(m,2H),4.44-4.50(m,1H),7.63(s,1H),8.32(s,1H),8.34(s,1H)；13C NMR(101MHz,MeOD)ppm19.86,25.25,28.30,48.61,67.88,77.35,113.35,115.83,128.44,137.09,140.18,145.22,147.53；HRMScalcd.for C13H15N3O3:261.1113,found：261.1099.
实施例2
在微波反应器中，向微波反应管中加入化合物1(0.8mmol)(E1)-N’(2-氟-4-甲基5-硝基-苯)-N,N-二甲基-甲脒【(E)-N'-(2-fluoro-4-methyl-5-nitrophenyl)-N,N-dimethylformamidine)】，干燥的1，2-丙二醇(2ml)，胺2d(4.0mmol)，反应混合物在微波反应器中170℃加热10min。用反相高效液相色谱法直接对反应混合物进行纯化,得到产物3d。产率为59％。
1H NMR(500MHz,MeOD)ppm 1.78(br.s.,4H),2.59(br.s., 4H),2.66(s,3H),2.90-3.02(m,2H),4.42(t,J＝6.71Hz,2H),7.58(s,1H),8.28(s,1H),8.35(s,1H)；13C NMR(126MHz,MeOD).ppm20.18,23.45,44.30,47.50,47.68,47.85,48.02,48.19,48.36,48.53,54.11,54.98,113.25,116.38,128.90,137.04,140.86,145.72,147.55；HRMS calcd.forC14H18N4O2:274.1430,found：274.1415.
实施例3
在微波反应器中，向微波反应管中加入化合物1(0.5mmol)(E1)-N’(2-氟-4-甲基5-硝基-苯)-N,N-二甲基-甲脒【(E)-N'-(2-fluoro-4-methyl-5-nitrophenyl)-N,N-dimethylformamidine)】，干燥的苄醇(4ml)，胺化合物2e(1.0mmol)，反应混合物在微波反应器中180℃加热15min。用反相高效液相色谱法直接对反应混合物进行纯化,得到产物3e。产率为67％。1H NMR(400MHz,MeOD).ppm 2.71(s,3H),3.72-3.81(m,2H),4.45-4.53(m,2H),7.63(s,1H),8.32(s,1H),8.33(s,1H)；13C NMR(101MHz,MeOD)ppm；HRMS calcd.forC11H13N3O3:235.0957,found 235.0567。
显然，以上所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
Claims (3)
1.1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物，其特征在于，其化合物的通式为：
其中：R为
2.1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物的制备方法，其特征在于，包括下述步骤:利用微波反应，采用以下反应合成得到以下通式中产物化合物3；
具体步骤为在微波反应器中，向微波反应管中加入0.4-0.8mmol化合物1(E1)-N’(2-氟-4-甲基5-硝基-苯)-N,N-二甲基-甲脒，2ml干燥的溶剂，3.0-5.0mmol胺2，反应混合物在微波反应器中110-180℃加热10-30min；用反相高效液相色谱法直接对反应混合物进行纯化,得到产物3。
3.根据权利要求2所述的1-烷烃-6-甲基-5-硝基-1H-苯并[D]咪唑类化合物的制备方法，其特征在于，所述溶剂为二甘醇、DMSO、DMF、1，2-丙二醇、乙二醇、苄醇、环丁砜的任一种。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107445899A (zh) * | 2017-07-19 | 2017-12-08 | 枣庄学院 | 一种苯并咪唑类化合物及其制备方法 |
| CN108863820A (zh) * | 2018-07-30 | 2018-11-23 | 枣庄学院 | 一种取代邻苯二胺的合成方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| US20200002291A1 (en) * | 2017-07-19 | 2020-01-02 | Engineering And Technology Institute Of Lunan Coal Chemical Engineering | Benzimidazole Compound and Preparation Method Thereof |
| JP2020518661A (ja) * | 2017-07-19 | 2020-06-25 | シャンドン ルーナン リサーチ インスティテュート オブ コール ケミカル エンジニアリング アンド テクノロジーＳｈａｎｄｏｎｇ Ｌｕｎａｎ Ｒｅｓｅａｒｃｈ Ｉｎｓｔｉｔｕｔｅ ｏｆ Ｃｏａｌ Ｃｈｅｍｉｃａｌ Ｅｎｇｉｎｅｅｒｉｎｇ ａｎｄ Ｔｅｃｈｎｏｌｏｇｙ | ベンゾイミダゾール系化合物およびその製造方法 |
| US10787420B2 (en) * | 2017-07-19 | 2020-09-29 | Shandong Engineering And Technology Institute Of Lunan Coal Chemical Engineering | Benzimidazole compound and preparation method thereof |
| CN108863820A (zh) * | 2018-07-30 | 2018-11-23 | 枣庄学院 | 一种取代邻苯二胺的合成方法 |
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| CN106946862B (zh) | 2019-09-03 |
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