One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K<sub>2</sub>CO<sub>3</sub> under microwave irradiation

Yucai ZENG; Xiaoling LIU; Qifeng LIANG; Jianquan LYU

doi:10.11949/j.issn.0438-1157.20181418

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One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K₂CO₃ under microwave irradiation

更新时间：2020-06-24

- One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K₂CO₃ under microwave irradiation
- CIESC Journal Issue S1, Pages: 110-114(2019)
- 作者机构：
  
  嘉应学院化学与环境学院，广东梅州 514015
- 作者简介：
- 基金信息：
- DOI：10.11949/j.issn.0438-1157.20181418
  CLC： O 625.6
- Received：27 November 2018，
  
  Revised：2018-12-11，
- 稿件说明：
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曾育才, 刘小玲, 梁奇峰, 吕鉴泉. 微波促进碳酸钾催化一锅法合成2-氨基-3氰基-4-芳基-4H-苯并色烯衍生物[J]. 化工学报, 2019, 70(S1): 110-114

ZENG Yucai, LIU Xiaoling, LIANG Qifeng, LYU Jianquan. One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K₂CO₃ under microwave irradiation[J]. CIESC Journal, 2019, 70(S1): 110-114 DOI: 10.11949/j.issn.0438-1157.20181418.
曾育才, 刘小玲, 梁奇峰, 吕鉴泉. 微波促进碳酸钾催化一锅法合成2-氨基-3氰基-4-芳基-4H-苯并色烯衍生物[J]. 化工学报, 2019, 70(S1): 110-114 DOI： 10.11949/j.issn.0438-1157.20181418.

ZENG Yucai, LIU Xiaoling, LIANG Qifeng, LYU Jianquan. One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K₂CO₃ under microwave irradiation[J]. CIESC Journal, 2019, 70(S1): 110-114 DOI: 10.11949/j.issn.0438-1157.20181418. DOI：

摘要

微波辐射下，乙醇溶剂中K

催化芳甲醛、丙二腈和

-萘酚（或

-萘酚）三组分一锅法快速合成了一系列2-氨基-3-氰基-4-芳基-4H-苯并[h]色烯或苯并[f]

色烯衍生物。以苯甲醛、丙二氰与

-萘酚的反应为模板反应，通过单因素实验方案优化了反应的工艺条件。结果表明：反应物各10 mmol，催化剂K

1 mmol，溶剂无水乙醇15 ml，采用微波功率500 W，80℃回流反应 5 min，2-氨基-3-氰基-4-苯基-4H-苯并[h]色烯（

）的收率83.6%。在上述最佳条件下，利用取代苯甲醛代替苯甲醛，4H-苯并[h]色烯衍生物(

)产率为65.8%~89.4%。利用

-萘酚代替

-萘酚，4H-苯并[f]色烯衍生物(

)产率为67.5%~82.9%，合成产物通过熔点和红外光谱表征其结构。

Abstract

A series of 2-amino-4-aryl-3-cyano-4H-benzo[h]chromene or benzo[h]

chromene derivatives were synthesized by a three-component one-pot reaction of aromatic aldehydes

malononitrile and

-naphthol(or

-naphthol) with K

as catalyst in anhydrous ethanol solvent under microwave irradiation. With benzaldehyde

malononitrile and

-naphthol as template reaction

the reaction conditions were optimized by single factor experiments. The results showed that 2-amino-4-aryl-3-cyano-4H-benzo[h]chromene(

) was obtained 83.6% yield with the condition of each reactant 10 mmol

1 mmol and anhydrous ethanol 15 ml as solvent

using microwave power 500 W

reflux reaction 5 min at 80℃. Under the best of the above conditions，using substituted benzaldehyde to replace benzaldehyde

4H-benzo[h]chromene derivatives(

) were obtained 65.8%~89.4% yield. Using

-naphthol to replace

-naphthol

4H-benzo[f]chromene derivatives(

) were obtained 67.5%~82.9% yield. The structures of these compound were characterized by m.p. and IR.

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references

黄邦洲 , 朱天民 , 于学君 , 等 . 2H-苯并吡喃类化合物的简便合成方法 [J]. 有机化学 , 1989 , 9 ( 6 ): 552 - 554 .

Huang B Z , Zhu T M , Yu X J , et al . A convenient route for the synthesis of 2H-1-benzopyranes [J]. Chinese Journal of Organic Chemistry , 1989 , 9 ( 6 ): 552 - 554 .

Goutam B , Bubun B ． Facile and one-pot access to diverse and densely functionalized -amino-3-cyano-4H-pyrans and pyran-annulated heterocyclic scaffolds via an ecofriendly multicomponent reaction at room temperature using urea as a novel organo-catalyst [J]. ACS Sustainable Chem . Eng ., 2014 , 2 : 411 - 422 .

Li W J , Liu H , Jiang X F , et al . Enantioselective organocatalytic conjugate addition of nitroalkanes to electrophilic 2-iminochromenes [J]. ACS Catal ., 2012 , 2 : 1535 - 1538 .

Kemn I W , Kasibhatla S , Jiang S . Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell and caspase-based high-throughput screening assay(2): Structure- activity relationships of the 7-and 5-, 6-, 8-positions [J]. Bioorganic & Medicinal Chemistry Letters , 2005 , 15 : 4745 - 4751 .

Kemn I W , Drewe J , Jiang S . Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell and caspase-based high-throughput screening assay structure-activity relationships of the 4-aryl group [J]. J. Med. Chem ., 2004 , 47 : 6299 - 6310 .

Zhang G , Zhang Y H , Yan J X , et al . One-pot enantioselective synthesis of functionalized pyranocoumarins and 2-amino-4H-chromenes: discovery of a type of potent antibacterial agent [J]. J. Org. Chem ., 2012 , 77 : 878 - 888 .

王喜存 , 许新兵 , 权正军 , 等 . PEG-400 为绿色反应介质无催化一锅法合成 2-氨基-3-氰基-4-芳基-4H-苯并色烯衍生物 [J]. 有机化学 , 2009 , 29 ( 11 ): 1821 - 1824 .

Wang X C , Xu X B , Quan Z J , et al . Synthesis of 2-amino-3-cyano-4-arylbenzochromenes under noncatalysis conditions using PEG-400 as green medium [J]. Chinese Journal of Organic Chemistry , 2009 , 29 ( 11 ): 1821 - 1824 .

周杰兴 , 王香善 , 曾兆森 , 等 . KF-Al 2 O 3 催化下二-γ-吡喃并[2,3-a;2',3'-f] 萘衍生物的合成 [J]. 有机化学 , 2007 , 27 ( 6 ): 786 - 789 .

Zhou J X , Wang X S , Zeng Z S , et al . Synthesis of di-γ-pyrano[2,3-a;2',3'-f]naphthalene derivatives catalyzed by KF/Al 2 O 3 [J]. Chinese Journal of Organic Chemistry , 2007 , 27 ( 6 ): 786 - 789 .

章明 , 张爱琴 , 黄仁生 , 等 . 无溶剂CTAB催化制备取代2-氨基-2-色烯 [J]. 化学试剂 , 2006 , 28 ( 8 ): 491 - 492 .

Zhang M , Zhang A Q , Huang R S , et al . CTAB catalyzed preparation of substituted 2-amino-2-chromene under solvent free condition [J]. Chemical Reagents , 2006 , 28 ( 8 ): 491 - 492 .

史达清 , 王香善 , 屠树江 . KF/ Al 2 O 3 催化下4H-色烯衍生物的合成 [J]. 有机化学 , 2002 , 22 ( 12 ): 1053 - 1056 .

Shi D Q , Wang X S , Tu S J . Synthesis of 4H-chromene derivatives catalyzed by KF/Al 2 O 3 [J]. Chinese Journal of Organic Chemistry , 2002 , 22 ( 12 ): 1053 - 1056 .

Saeed B , Sorour R , Morteza B , et al . DABCO-catalyzed efficient synthesis of naphthopyran derivatives via one-pot three component condensation reaction at room temperature [J]. Synthetic Commun , 2008 , 38 : 1078 - 1089 .

孙宏伟 , 王浩宇 , 连春霞 , 等 . DABCO催化的“一锅法”水相合成苯并色烯衍生物 [J]. 合成化学 , 2011 , 19 ( 3 ): 370 - 372 .

Sun H W , Wang H Y , Lian C X , et al . DABCO-catalyzed synthesis of benzo[g]chromene derivatives in water by one-pot method [J]. Chinese Journal of Synthetic Chemistry , 2011 , 19 ( 3 ): 370 - 372 .

陈路 , 李毅群 , 黄旭江 , 等 . 乙二胺四乙酸四钠“一锅法”催化合成2-氨基-2-色烯衍生物 [J]. 有机化学 , 2009 , 29 ( 3 ): 437 - 440 .

Chen L , Li Y Q , Huang X J , et al . One-pot synthesis of 2-amino-2-chromenes catalyzed by tetrasodium ethylenediaminetetraacetate [J]. Chinese Journal of Organic Chemistry , 2009 , 29 ( 3 ): 437 - 440 .

Khurana J M , Nand B , Saluja P . DBU: a highly efficient catalyst for one-pot synthesis of substituted 3,4-dihydropyrano［3,2-c］chromenes, dihydropyrano［4,3-b］pyranes, 2-amino-4H-benzo［h］chromenes and 2-a-mino-4H-benzo[g]chromenes in aqueous medium [J]. Tetrahedron , 2010 , 66 : 5637 - 5641 .

Seyed M B , NiloufarI R , Hamed T . Nanozeoliteclino ptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives inaqueous media [J]. Green Chem ., 2013 , 15 : 3446 - 3458 .

Dekamin M G , Eslami M . Highly efficient organo catalytic synthesis of diverse and densely functionalized 2-amino-3-cyano-4H-pyrans under mechanochemical ball milling [J]. Green Chem ., 2014 , 16 : 4914 - 4921 .

Nourallah H , Malek T M , Mir R M , et al . Potassium sodium tartrate as a versatile and efficient catalyst for the one-pot synthesis of pyran annulated heterocyclic compounds in aqueous media [J]. Res . Chem . Intermed ., 2015 , 41 : 169 - 174 .

窦辉 , 高思旖 , 付召龙 , 等 . 新型氨基功能化碱性离子液体1-(2-氨基乙基)-3-甲基咪唑咪唑盐催化四类取代2-氨基-4H-色烯衍生物的合成 [J]. 有机化学 , 2011 , 31 ( 7 ): 1056 - 1063 .

Dou H , Gao S Y , Fu Z L , et al . Improved synthesis of substituted 2-amino-4H-chromene derivatives catalyzed by a new amino-functionalized basic ionic liquid 1-(2-aminoethyl)-3-methylimidazolium imidazolide [J]. Chinese Journal of Synthetic Chemistry , 2011 , 31 ( 7 ): 1056 - 1063 .

王英磊 , 陈靖 , 王玉东 , 等 . 低毒、易降解离子液体三乙醇胺乙酸盐催化合成2-氨基-4H-苯并色烯衍生物 [J]. 南阳理工学院学报 , 2017 , 9 ( 2 ): 99 - 103 .

Wang Y L , Chen J , Wang Y D , et al . Synthesis of 2-amino-4H-benzochromene derivatives by low toxic and readily-biodegradable ionic liquid triethanolammonium acetate [J]. Journal of Nanyang institute of Technology , 2017 , 9 ( 2 ): 99 - 103 .

Mithu S , Babulal D , Amarta K P . Synthesis of pyran derivatives under ultrasound irradiation using Ni nanoparticles as reusable catalysts in aqueous medium [J]. Comptes Rendus Chimie , 2013 , 16 : 1079 - 1085 .

李佰林 , 李红艳 , 程优 . 酸性离子液体催化2-氨基-2-色烯的高能球磨法合成 [J]. 化学试剂 , 2014 , 36 ( 11 ): 1045 - 1049 .

Li B L , Li H Y , Cheng Y . Efficient synthesis of 2-amino-2-chromenes by high energy ball milling catalysized by acidic ionic

liquids [J]. Chemical Reagents , 2014 , 36 ( 11 ): 1045 - 1049 .

栾长军 , 王建强 , 张国华 , 等 . 无催化剂条件下微波辐射一步法合成2-氨基-4-芳基-5-氧代-5,6,7,8-四氢-4H-苯并吡喃-3-腈 [J]. 有机化学 , 2011 , 31 ( 6 ): 860 - 864 .

Luan C J , Wang J Q , Zhang G H , et al . One-pot synthesis of 2-amino-4-aryl-5-oxo-5,6,7,8-tetrahydro-4H-benzopyran-3- carbonitrile under microwave irradiation without catalyst [J]. Chinese Journal of Organic Chemistry , 2011 , 31 ( 6 ): 860 - 864 .

曾育才 , 刘小玲 , 温运明 , 等 . K 2 CO 3 催化合成2-氨基-4H-色烯衍生物 [J]. 精细化工 , 2014 , 31 ( 12 ): 1522 - 1525 .

Zeng Y C , Liu X L , Wen Y M , et al . Synthesis of 2-amino-4H-chromene derivatives catalyzed by K 2 CO 3 [J]. Fine Chemicals , 2014 , 31 ( 12 ): 1522 - 1525 .

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⁰

One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K2CO3 under microwave irradiation

DOI：10.11949/j.issn.0438-1157.20181418

摘要

Abstract

关键词

Keywords

references

One-pot synthesis of 2-amino-4-aryl-3-cyano-4H-benzochromene derivatives catalyzed by K₂CO₃ under microwave irradiation