CN112574219A - 一种苯并咪唑并嘧啶酮衍生物的合成方法 - Google Patents
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- KMSZDHZYWPIJAC-UHFFFAOYSA-N imidazo[4,5-f]quinazolin-2-one Chemical class C1=NC=C2C3=NC(=O)N=C3C=CC2=N1 KMSZDHZYWPIJAC-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000001308 synthesis method Methods 0.000 title description 4
- 150000004698 iron complex Chemical class 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- TZEMTMCOYZMUSN-UHFFFAOYSA-N 1H-benzimidazole 1H-pyrimidin-2-one Chemical class O=C1N=CC=CN1.C1=CC=C2NC=NC2=C1 TZEMTMCOYZMUSN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims abstract description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 claims abstract description 3
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 5
- 229940126062 Compound A Drugs 0.000 claims description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229940044631 ferric chloride hexahydrate Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- -1 trichloromethyl-substituted benzimidazolopyrimidinone Chemical class 0.000 description 3
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
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- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
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- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XPPWAISRWKKERW-UHFFFAOYSA-N copper palladium Chemical compound [Cu].[Pd] XPPWAISRWKKERW-UHFFFAOYSA-N 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
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- HULWKEZTVNNHQB-UHFFFAOYSA-N disodium methanol sulfide Chemical class CO.[S-2].[Na+].[Na+] HULWKEZTVNNHQB-UHFFFAOYSA-N 0.000 description 1
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明通过溶剂热反应快速实现了苯并咪唑并嘧啶酮衍生物的铁配合物的制备,进而向铁配合物中加硫化钠去除FeCl2后得到结构通式(I)所示的苯并咪唑并嘧啶酮衍生物,本发明合成周期短,分离提纯的步骤少,减少了有机溶剂的使用,有较高的应用价值。
Description
技术领域
本发明涉及一种苯并咪唑并嘧啶酮衍生物的合成方法,属于合成技术领域。
背景技术
嘧啶酮类化合物可作为钙通道阻滞剂,抗高血压,抗癌等药物,由于它们的药物特性,嘧啶酮的合成引起了广泛关注。在已报道的合成方法中,苯并咪唑类衍生物与取代的异氰酸酯进行[3+3]环加成得到三氟甲基或三氯甲基取代的苯并咪唑并嘧啶酮衍生物。但上述反应中通常使用腐蚀性、毒性较强的试剂,限制了嘧啶酮及其衍生物的合成及应用,急需开发新型无毒,条件温和的合成方法。
发明内容
本发明的目的是提供一种苯并咪唑并嘧啶酮衍生物的制备方法。
本发明实现过程如下:
一种苯并咪唑并嘧啶酮衍生物的合成方法,包括以下步骤:
(1)将化合物A与化合物B溶于有机溶剂中,加入六水合三氯化铁,在密闭反应器中于120~160 ℃反应得到化合物C所示铁配合物,
R选自氢、卤素基、C1-C3的烷基、C1-C3的烷氧基、硝基;
(2)向化合物C所示铁配合物中加硫化钠去除FeCl2后得到结构通式(I)所示的苯并咪唑并嘧啶酮衍生物,
上述步骤(1)中,化合物A、化合物B和六水合三氯化铁的摩尔比为2:2:1。
上述步骤(1)中,有机溶剂为甲醇、乙醇或乙腈。
上述步骤(1)中,反应温度为120~160 ℃。
本发明的优点:本发明通过溶剂热反应快速实现了苯并咪唑并嘧啶酮衍生物的铁配合物的制备,进而可以制备得到苯并咪唑并嘧啶酮衍生物。合成周期短,分离提纯的步骤少,减少了有机溶剂的使用,有较高的应用价值。
附图说明
图1为化合物1的结构图;
图2为化合物1的热重图;
图3为化合物1的粉末衍射图;
图4 为化合物1的XPS 图;
图5为化合物1的单晶质谱图;
图6为化合物1的红外光谱图;
图7为化合物1的生成过程推测机理图。
具体实施方式
为了更清楚的理解发明,以下通过发明人给出的依本发明技术方案所完成的具体实施例对本发明进一步的详细描述。
实施例1:化合物1(R= H)的合成及结构分析
将0.2 mmol的S,S-1,2-双-(1-甲基-2-苯并咪唑)-1,2-乙二醇衍生物(64.5 mg)和0.2 mmol(1-甲基-1H-苯并[d]咪唑-2-基)甲胺(32.2 mg)加入到容积为25.0 mL的聚四氟乙烯的反应釜中,加入10.0 mL的乙醇溶解后,再加入0.1 mmol的六水合三氯化铁(26.8mg),搅拌5分钟,密封,放入140 ℃的烘箱中反应48 h,然后保持10℃ / h缓慢冷却至室温,得到红色晶体(化合物1)和红褐色母液,红色晶体产率25%。
图1为化合物1的单晶结构图,其最小不对称单元是LFeCl2, 属于三斜晶系,空间群是P-1,Fe的配位环境是N2Cl2, 四面体配位,晶胞参数为a = 7.9479(3) Å,b = 8.8239(4) Å,c = 14.1708(6) Å,α = 81.431(4) o,β = 85.810(3) o,γ = 67.237(4)o。其结构是由苯并咪唑并嘧啶酮三个杂环构成,其中N3是苯并咪唑环上的N原子,另一个N1来自嘧啶酮的N原子,该六元环与苯并咪唑环共平面,通过这个三并环的13个环上的原子的最小二乘面的距离最长的是N2(0.26 Å)。C1-O1键长为1.216(3) Å,表明为C=O,且键角O1-C1-N2(119.04(19)˚), O1-C1-N2 (125.44(19)˚),和N1-C1-N2 (115.44(17)˚)之和为359.9˚,表明C1为sp2杂化。六元环中的4个C-N键长介于C-N单键和双键之间,而且两个C-C键长介于C-C单键和双键之间,表明键长平均化。
图2为化合物1的热重图,化合物1的晶体在225℃才开始失重,证明没有客体分子的存在,烧至600℃失重57% 左右,证明化合物1的稳定性。
图4为化合物1的XPS图,判定Fe的价态为正二价。
图5为化合物L1的电喷雾离子化高分辨质谱图。m/z在330.1334 处的峰归属为化合物的分子离子峰[L-FeCl2+H]+。
图6为化合物1的红外光谱谱图,C=O的伸缩振动峰在1715 cm-1,N-CH3的伸缩振动峰在1426 cm-1。
图7 为该化合物1的生成机理图,通过控制实验分离得到中间体a-2和f,并获得了晶体结构,高分辨质谱跟踪捕捉到了中间体a-2、e、f、g。基于此,反应可能的路径是,a-1与Fe3+配位得到a-2,脱水得到c, c与b反应经d得到e,空气氧化e得到f,然后发生酰基取代得到化合物1和g。
将制备得到的化合物1溶解于二氯甲烷,加入饱和硫化钠甲醇溶液,搅拌3 小时,过滤、浓缩、重结晶得到如下化合物:5-甲基-3-(1-甲基-1H-苯并[d]咪唑-2-基)苯并[4,5]咪唑并[1,2-c]嘧啶-1(5H)-酮,
实施例2:
发明人通过改变原料,制备得到了系列苯并咪唑并嘧啶酮衍生物铁配合物,具体见表1所示。
实验测试部分:
1. 化合物的结构图:化合物1的X射线单晶衍射测定在Rigaku R-AXIS SPIDER IPdiffractometer单晶衍射仪上进行(CuKα , λ = 1.54184 Å)。
2. 热重图:室温下称取6 mg的L,在Netzsch TG209F3上进行L热稳定测试,其中加热区间为30-800 oC,升温速率为10 oC/min,氮气流速为15 mL/min。
3. 粉末衍射(P XRD)图:粉末X射线衍射是在Rigaku Smart Lab3KW衍射仪上进行的,采用的是铜钯并以5 o/min的扫数在2θ 范围为3-65o之间进行测试。
4. XPS图:取15.0 mg的L在单色全X-射线源在Escalab250Xi上进行X-射线光电子能谱(XPS)。
5. 高分辨质谱图:室温下,取1颗单晶溶于色谱级乙腈中,在Thermo ExactivePlus ESI-MS 上进行阳离子模式下的数据采集。
6. 红外光谱:室温下,在Bruker FTIR spectrophotometer上进行L的红外测试,取0.1 mg的L制成KBr压片,测试范围为4000-400 cm-1。
Claims (4)
2.根据权利要求1所述苯并咪唑并嘧啶酮衍生物的合成方法,其特征在于:步骤(1)中,化合物A、化合物B和六水合三氯化铁的摩尔比为2:2:1。
3.根据权利要求1所述苯并咪唑并嘧啶酮衍生物的合成方法,其特征在于:步骤(1)中,有机溶剂为甲醇、乙醇或乙腈。
4.根据权利要求1所述苯并咪唑并嘧啶酮衍生物的合成方法,其特征在于:步骤(1)中,反应温度为120~160 ℃。
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CA2028530A1 (en) * | 1989-11-21 | 1991-05-22 | Christian Hubschwerlen | Substituted pyrimidobenzimidazole derivatives |
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