Solvent-Free Synthesis of Pyrrolo [2,1-α] Isoquinolines via One-Pot Four-Component Reaction

被引：2

作者：

Aminkhani, Ali ^{[1
]}

Sharifi, Sina ^{[2
,3
]}

机构：

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

[2] Harvard Med Sch, Massachusetts Eye & Ear, Dept Ophthalmol, Boston, MA 02115 USA

[3] Harvard Med Sch, Schepens Eye Res Inst, Boston, MA 02115 USA

来源：

LETTERS IN ORGANIC CHEMISTRY | 2022年 / 19卷 / 03期

关键词：

pyrrolo [2,1-a]isoquinoline; four-component reactions; isoquinoline; isocyanide; aromatic aldehydes; solvent-free synthesis; BRAIN DELIVERY; LAMELLARIN-D; DERIVATIVES; ALKALOIDS; CHEMISTRY; CHIRALITY; HYBRIDS; NMR;

D O I：

10.2174/1570178618666210805103552

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient four-component reaction to synthesize pyrrolo [2,1-a] isoquinolines from malononitrile, aromatic aldehydes, isoquinoline, and cyclohexyl isocyanide under solvent-free conditions is described. In a convenient, simple, and efficient one-pot procedure, the domino Knoevenagel-nucleophilic cycloaddition reaction affords excellent yields of products in less than 1 h.

引用

页码：244 / 249

页数：6

共 57 条

[21] Tungstic acid-functionalized MCM-41 as a novel mesoporous solid acid catalyst for the one-pot synthesis of new pyrrolo[2,1-a]isoquinolines [J].

Karami, Bahador ;

Farahi, Mahnaz ;

Akrami, Sedigheh ;

Elhamifar, Dawood .

NEW JOURNAL OF CHEMISTRY, 2018, 42 (15) :12811-12816

[22] NHC-Mediated Synthesis of Pyrrolo[2,1-a]isoquinolines and Their Photophysical Investigations [J].

Krishnan, Jagadeesh ;

Vedhanarayanan, Balaraman ;

Sasidhar, B. S. ;

Varughese, Sunil ;

Nair, Vijay .

CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (06) :623-627

[23] SYNTHESIS OF 2-(3-COUMARINYL)PYRROLO[2,1-a[ISOQUINOLINE DERIVATIVES BY THE CHICHIBABIN REACTION [J].

Kulikova, Yu. A. ;

Surikova, O. V. ;

Mikhailovskii, A. G. ;

Vakhrin, M. I. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (03) :290-293

[24] Mild and General Synthesis of Pyrrolo[2,1-a]isoquinolines and Related Polyheterocyclic Frameworks from Pyrrole Precursors Derived from a Mechanochemical Multicomponent Reaction [J].

Leonardi, Marco ;

Villacampa, Mercedes ;

Menendez, J. Carlos .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (05) :2570-2578

[25] Total Synthesis of Lamellarins D, H, and R and Ningalin B [J].

Li, Qingjiang ;

Jiang, Jingqian ;

Fan, Aili ;

Cui, Yuxin ;

Jia, Yanxing .

ORGANIC LETTERS, 2011, 13 (02) :312-315

[26] Synthesis and neurotropic activity of novel quinoline derivatives [J].

Lukevics, E ;

Segal, I ;

Zablotskaya, A ;

Germane, S .

MOLECULES, 1997, 2 (12) :180-185

[27] Recurrent π-π stacking motifs in three new 4,5-dihydropyrazolyl-thiazole-coumarin hybrids: X-ray characterization, Hirshfeld surface analysis and DFT calculations [J].

Madni, Murtaza ;

Ahmed, Muhammad Naeem ;

Hafeez, Muhammad ;

Ashfaq, Muhammad ;

Tahir, Muhammad Nawaz ;

Gil, Diego M. ;

Galmes, Bartomeu ;

Hameed, Shahid ;

Frontera, Antonio .

NEW JOURNAL OF CHEMISTRY, 2020, 44 (34) :14592-14603

[28] 1,2-dihydrolsoquinoline-N-acetic acid derivatives as new carriers for specific brain delivery I: Synthesis and estimation of oxidation kinetics using multivariate calibration method. [J].

Mahmoud, S ;

Aboul-Fadl, T ;

Sheha, M ;

Farag, H ;

Mouhamed, AMI .

ARCHIV DER PHARMAZIE, 2003, 336 (12) :573-584

[29]

Malipeddi H., 2011, Int. J. Res. Ayurveda Pharm, V2, P1079, DOI DOI 10.7897/2277-4343.0611

[30] Molecular determinants of topoisomerase I poisoning by lamellarins: Comparison with camptothecin and structure-activity relationships [J].

Marco, E ;

Laine, W ;

Tardy, C ;

Lansiaux, A ;

Iwao, M ;

Ishibashi, F ;

Bailly, C ;

Gago, F .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (11) :3796-3807

← 1 2 3 4 5 6 →