CN106220611A - 2‑(1h‑吲哚‑3‑基)‑1h‑苯并咪唑衍生物的新制备方法 - Google Patents
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- QXJMCSBBTMVSJS-UHFFFAOYSA-N 1-(1h-indol-2-yl)ethanone Chemical compound C1=CC=C2NC(C(=O)C)=CC2=C1 QXJMCSBBTMVSJS-UHFFFAOYSA-N 0.000 description 2
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- YWPCKFXXPPYHKG-UHFFFAOYSA-N 2-(5-bromo-1H-indol-3-yl)-1H-benzimidazole Chemical compound Brc1ccc2[nH]cc(-c3nc4ccccc4[nH]3)c2c1 YWPCKFXXPPYHKG-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- JVZMBSGNSAHFCY-UHFFFAOYSA-N 5-bromo-1h-indole-3-carboxylic acid Chemical compound C1=C(Br)C=C2C(C(=O)O)=CNC2=C1 JVZMBSGNSAHFCY-UHFFFAOYSA-N 0.000 description 1
- RVVSEZGJCOAUED-UHFFFAOYSA-N 5-methoxy-1h-indole-3-carboxylic acid Chemical compound COC1=CC=C2NC=C(C(O)=O)C2=C1 RVVSEZGJCOAUED-UHFFFAOYSA-N 0.000 description 1
- 229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
一种由下述通式表示的2‑(1H‑吲哚‑3‑基)‑1H‑苯并咪唑衍生物:其中,式中取代基R1、R2、R3、R4、R5、R6、R8、R9、R10为甲基,乙基,丙基,卤素等取代基。本发明涉及一种2‑(1H‑吲哚‑3‑基)‑1H‑苯并咪唑衍生物的新制备方法,合成步骤主要包括:以吲哚‑3‑甲酸及其衍生物和邻苯二胺及其衍生物为起始原料,在溶剂中经催化剂催化一步反应得目标产物。该方法具有易操作,省时,易纯化,产率高等优点。
Description
技术领域
本发明涉及有机合成技术领域,具体涉及到一种2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物的新制备方法。
背景技术
吲哚和苯并咪唑类化合物是一类重要的杂环衍生物,由于吲哚类化合物在在工业、农业和医药领域显示出广泛的用途,所以近年来受到越来越多的关注。其次,含吲哚结构的生物碱在生物体内显示出多种生物活性作用,尤其是表现出抗肿瘤活性,为此也成为杂环化合物研究的热点。
Biradar J S等(MK-10Clay–Catalyzed Synthesis of 2-(2′,5′-Disubstituted-1′H-indol-3′-yl)-1H-benzo[d]imidazoles under Conventional andMicrowave Irradiation.Synthetic Communications,2011,41(6):885-890.)提出了一种以取代邻苯二胺和2,5-二取代-3-氰乙酰基吲哚分别在传统加热和微波法条件下合成2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其中传统加热反应收率为51%~63%,微波法收率为75%~92%,但反应中的原料2,5-二取代-3-氰乙酰基吲哚不易制备且收率低。微波法本身存在的固有缺陷使得这种方法难以用于较大规模的工业化生产。
Chari M A等(Room temperature synthesis of benzimidazole derivativesusing reusable cobalt hydroxide(II)and cobalt oxide(II)as efficient solidcatalysts.Tetrahedron Letters,2011,52(43):5575-5580.)提出了一种以邻苯二胺和吲哚-3-甲醛在Co(OH)2/CoO催化下以乙醇作溶剂合成2-(1H-吲哚-3-基)-1H-苯并咪唑,产率达80%以上。但钴类化合物本身毒性大,此方法在生成目标产物的同时,还会生成N-取代副产物,目标产物需经过柱层析分离才能得到,后处理繁琐。
发明内容
为解决上述问题,本发明的目的是提供一种操作简单,产率较高,对生产条件要求不高的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物新合成方法。
一种由下述通式表示的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物:
其中,式中取代基R1可以为—H,—CH3,—CH2CH3,—CH2CH2CH3,—CH(CH3)2,—CH2CH=CH2,—CH2Ph,—COCH3,—CONHCH3,p-CH3-C6H4-SO2—;R2、R3、R4、R5、R6、R8、R9、R10可以为—H,—CH3,—CH2CH3,—CHCH=CH2,—CH2Ph,—COCH3,—CF3,—CCl3,—CN,—NHCH3,—NO2,—OCH3,—CH2NH2,—COOCH3,—CONHCH3。
本发明方法的步骤主要包括:以吲哚-3-甲酸及其衍生物和邻苯二胺及其衍生物为起始原料,在溶剂中经催化剂催化一步反应得到目标产物。
其特征在于,取代邻苯二胺与取代吲哚-3-甲酸的摩尔比为1:0.5~3。
上述方案中,反应温度为50~200℃。
上述方案中,反应时间为1~9小时。
上述方案中,后处理时,反应液于冰浴条件下加碱调节pH至7~12,所得粗品用乙醇重结晶得目标产品。
本发明与现有技术相比,其优点和有益效果在于:反应原料取代吲哚-3-甲酸和取代邻苯二胺易得,对反应条件的要求低,收率高,所用试剂成本低,实验操作和后处理简单。
具体实施方式
现将对本发明的具有代表性的实施方案进行举例说明,仅仅是示例性的说明,通过下述实施例将有助于理解本发明,但所举实例并不限制本发明的范围。
实施例1:向100mL三口瓶中加入1.61g吲哚-3-甲酸,40mL丙三醇,10mL磷酸,开启搅拌,室温下分批次加入1.08g邻苯二胺,升温至160℃,反应4h。待反应完毕,冰浴条件下,用20%的氢氧化钠溶液调至pH=8,抽滤,滤饼用无水乙醇重结晶,干燥得2-(1H-吲哚-3-基)-1H-苯并咪唑,产率83.5%。
实施例2:向100mL三口瓶中加入,2.05吲哚-3-甲酸,45mL乙二醇,12mL多聚磷酸,开启搅拌,室温下分批次加入1.22g 4-甲基邻苯二胺,升温至180℃,反应3h。待反应完毕,冰浴条件下,用20%的氢氧化钠溶液调至pH=9,抽滤,滤饼用无水乙醇重结晶,干燥得2-(1H-吲哚-3-基)-5-甲基-1H-苯并咪唑,产率82.9%。
实施例3:向100mL三口瓶中加入,2.85g 5-甲氧基吲哚-3-甲酸,50mL二苯醚,10mL冰醋酸,开启搅拌,室温下分批次加入1.53g 4-硝基邻苯二胺,升温至190℃,反应6h。待反应完毕,冰浴条件下,用20%的氢氧化钠溶液调至pH=8,抽滤,滤饼用无水乙醇重结晶,干燥得2-(5-甲氧基-1H-吲哚-3-基)-5-硝基-1H-苯并咪唑,产率78.1%。
实施例4:向100mL三口瓶中加入,1.36g 5-溴吲哚-3-甲酸,30mL硝基苯,8mL多聚磷酸,开启搅拌,室温下分批次加入0.96g邻苯二胺,升温至回流,反应3.5h。待反应完毕,冰浴条件下,用20%的氢氧化钠溶液调至pH=10,抽滤,滤饼用无水乙醇重结晶,干燥得2-(5-溴-1H-吲哚-3-基)-1H-苯并咪唑,产率82.3%。
实施例5:向100mL三口瓶中加入,2.44g N-甲基吲哚-3-甲酸,40mL乙二醇,9mL稀硫酸,开启搅拌,室温下分批次加入1.05g邻苯二胺,升温至回流,反应4.5h。待反应完毕,冰浴条件下,用20%的氢氧化钠溶液调至pH=8,抽滤,滤饼用无水乙醇重结晶,干燥得2-(N-甲基-1H-吲哚-3-基)-1H-苯并咪唑,产率78.4%。
Claims (8)
1.一种由下述通式表示的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物的新制备方法,以吲哚-3-甲酸及其衍生物和邻苯二胺及其衍生物为起始原料,在溶剂中经催化剂催化一步反应得到目标产物。
2.根据权利要求1中所述,式中取代基R1可以为—H,—CH3,—CH2CH3,—CH2CH2CH3,—CH(CH3)2,—CH2CH=CH2,—CH2Ph,—COCH3,—CONHCH3,p-CH3-C6H4-SO2—;R2、R3、R4、R5、R6、R8、R9、R10可以为—H,—CH3,—CH2CH3,—CHCH=CH2,—CH2Ph,—COCH3,—CF3,—CCl3,—CN,—NHCH3,—NO2,—OCH3,—CH2NH2,—COOCH3,—CONHCH3。
3.根据权利要求1中所述的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其制备方法的特征在于,溶剂可为丙三醇、乙二醇、二苯醚和硝基苯。
4.根据权利要求1中所述的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其制备方法的特征在于,催化剂可以为磷酸、硫酸、多聚磷酸和冰醋酸。
5.根据权利要求1所述的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其制备方法的特征在于,取代邻苯二胺与取代吲哚-3-甲酸的摩尔比为1:0.5~3。
6.根据权利要求1所述的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其制备方法的特征在于,反应温度为50~200℃。
7.根据权利要求1所述的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其制备方法的特征在于,,反应时间为1~9小时。
8.根据权利要求1所述的2-(1H-吲哚-3-基)-1H-苯并咪唑衍生物,其制备方法的特征在于,后处理时,反应液于冰浴条件下加碱调节pH至7~12,所得粗品用乙醇重结晶得目标产品。
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