A clean, simple and efficient synthesis of trans-[3-(aryl)-2,3-dihydrofuro[3,2-h]quinolin-2-yl]-(4-chlorophenyl)methanones

被引：0

作者：

Salari, Maryam ^{[1
]}

Hassanabadi, Alireza ^{[2
]}

Mosslemin, Mohammad H. ^{[1
]}

机构：

[1] Islamic Azad Univ, Yazd Branch, Dept Chem, Yazd, Iran

[2] Islamic Azad Univ, Zahedan Branch, Dept Chem, Zahedan, Iran

来源：

JOURNAL OF CHEMICAL RESEARCH | 2017年 / 07期

关键词：

8-hydroxyquinoline; choline hydroxide; green chemistry; multi-component reaction; aromatic aldehydes; 4-chlorophenacyl bromide; 1,3-DICARBONYL COMPOUNDS; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; DIPOLAR CYCLOADDITION; DIHYDROFURANS; DERIVATIVES; REGIO;

D O I：

10.3184/174751917X14967701767058

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a green and efficient method for the synthesis of trans-[3-(aryl)-2,3-dihydrofuro[3,2-h]quinolin-2-yl]-(4-chlorophenyl)methanones from the condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 8-hydroxyquinoline and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water at reflux conditions. This new protocol employing choline hydroxide, which is a green and inexpensive catalyst, offers advantages such as mild reaction conditions, short reaction time, high yields and does not involve any hazardous solvent. Therefore, this procedure can be classified as green chemistry.

引用

页码：380 / 383

页数：4

共 25 条

[1] Synthesis of benzoindolizine derivatives by reaction of trimethyl phosphite, dialkyl acetylenedicarboxylates and isoquinolinium or quinolinium bromides [J].

Anary-Abbasinejad, Mohammad ;

Charkhati, Khadije ;

Hassanabadi, Alireza .

JOURNAL OF CHEMICAL RESEARCH, 2009, (02) :95-97

[2] Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions [J].

Arai, S ;

Nakayama, K ;

Suzuki, Y ;

Hatano, K ;

Shioiri, T .

TETRAHEDRON LETTERS, 1998, 39 (52) :9739-9742

[3] A highly stereoselective synthesis of 2,3,4,5-tetrasubstituted-trans-2,3-dihydrofurans [J].

Cao, WG ;

Ding, WY ;

Chen, J ;

Chen, YL ;

Zang, Q ;

Chen, GD .

SYNTHETIC COMMUNICATIONS, 2004, 34 (09) :1599-1608

[4] Pyridinium ylides in the synthesis of 2,3-dihydrofurans [J].

Chuang, CP ;

Tsai, AI .

SYNTHESIS-STUTTGART, 2006, (04) :675-679

[5] Asymmetric synthesis of 2,3-dihydrofurans by reaction of rhodium-stabilized vinylcarbenoids with vinyl ethers [J].

Davies, HML ;

Ahmed, G ;

Calvo, RL ;

Churchill, MR ;

Churchill, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2641-2645

[6]

Dean F.M., 1984, Comprehensive Heterocyclic Chemistry, V4, P531, DOI [10.1016/B978-008096519-2.00060-6, DOI 10.1016/B978-008096519-2.00060-6]

[7] Tandem nucleophilic reaction of 1,3-dicarbonyl compounds to methyl alpha-bromoacrylate: [3+2]heteroannulation leading to hydrofuran derivatives [J].

Hagiwara, H ;

Sato, K ;

Suzuki, T ;

Ando, M .

TETRAHEDRON LETTERS, 1997, 38 (12) :2103-2106

[8] NEW ROUTE TO 5-SUBSTITUTED RESORCINOLS AND RELATED SYSTEMS [J].

JAXACHAMIEC, AA ;

SAMMES, PG ;

KENNEWELL, PD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (01) :170-175

[9] Synthesis of enantiopure substituted dihydrofurans via the reaction of (S)-glyceraldehyde acetonide- or Garner aldehyde acetonide-derived enones with sulfonium ylides [J].

Jiang, YW ;

Ma, DW .

TETRAHEDRON-ASYMMETRY, 2002, 13 (10) :1033-1038

[10]

Jimenez-Gonzalez C., 2011, Green chemistry and engineering: a practical design approach

← 1 2 3 →