Four-Component Construction of Coumarin-Fused Pyrrolo[2,1-a]isoquinoline: Expedient Synthesis of Lamellarins and Their Regioselective Demethylation

被引：13

作者：

Manjappa, Kiran B. ^{[1
]}

Jhang, Jia-Wei ^{[2
]}

Lakshmi, K. C. Seetha ^{[2
]}

Yang, Ding-Yah ^{[1
,2
]}

机构：

[1] Tunghai Univ, Grad Program Biomed & Mat Sci, 1727,Sec 4,Taiwan Blvd, Taichung 407224, Taiwan

[2] Tunghai Univ, Dept Chem, 1727,Sec 4,Taiwan Blvd, Taichung, Taiwan

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 11卷 / 01期

关键词：

1,3-Dipolar cycloaddition; Lamellarin; Multi-component reaction; Pyrrolo[2; 1-a]isoquinoline; Regioselective demethylation; ALPHA; 20-SULFATE; TOPOISOMERASE-I; DERIVATIVES; INHIBITOR; CASCADE; CYCLOADDITION; ALKALOIDS; ALKENES; CORE;

D O I：

10.1002/ajoc.202100659

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Construction of the coumarin-fused pyrrolo[2,1-a]isolquinoline skeleton was realized through a four-component reaction between isoquinoline, ethyl bromoacetate, o-hydroxybenzaldehyde and nitromethane. This methodology was further extended to the synthesis of lamellarin D trimethyl ether and a formal synthesis of lamellarin D. The controlled demethylation of lamellarin D trimethyl ether yielded dihydroxy and tetrahydroxy lamellarin analogues regioselectively.

引用

页数：7

共 50 条

[31] Novel synthesis of pyrrolo[2,1-a]-isoquinoline using the reaction of isoquinolinium salts with active methylene compounds
Fujita, R
Watanabe, N
Tomisawa, H
HETEROCYCLES, 2001, 55 (03) : 435 - 438
[32] Divergent and Nucleophile-Assisted Rearrangement in the Construction of Pyrrolo[2,1-b][3]benzazepine and Pyrido[2,1-a]isoquinoline Scaffolds
Obydennik, Arina Y.
Titov, Alexander A.
Listratova, Anna V.
Borisova, Tatiana N.
Sokolova, Irina L.
Rybakov, Victor B.
Van der Eycken, Erik V.
Voskressensky, Leonid G.
Varlamov, Alexey V.
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (03)
[33] Cyclopropenones in the synthesis of indolizidine, pyrrolo[2,1-a] isoquinoline and indolizino[8,7-b]indole alkaloids
Jamshaid, Faisal
Kondakal, Vishnu V. R.
Newman, C. Declan
Dobson, Rhianne
Joao, Heidi
Rice, Craig R.
Mwansa, Joseph M.
Thapa, Bimod
Hemming, Karl
TETRAHEDRON, 2020, 76 (45)
[34] SYNTHESIS OF 1,3-DISUBSTITUTED-PYRROLO[2,1-A]ISOQUINOLINE-2-CARBOXYLIC ACIDS, ESTERS AND AMIDES
BRIDGE, AW
FENTON, G
HALLEY, F
HURSTHOUSE, MB
LEHMANN, CW
LYTHGOE, DJ
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (22): : 2761 - 2772
[35] Catalytic Asymmetric Tandem Reaction of Tertiary Enamides: Expeditious Synthesis of Pyrrolo[2,1-a]isoquinoline Alkaloid Derivatives
Xu, Xin-Ming
Zhao, Liang
Zhu, Jieping
Wang, Mei-Xiang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (11) : 3799 - 3803
[36] Solvent-Free Synthesis of Pyrrolo [2,1-α] Isoquinolines via One-Pot Four-Component Reaction
Aminkhani, Ali
Sharifi, Sina
LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (03) : 244 - 249
[37] Synthesis of isoquinoline derivatives of quinoxalin-2-one from pyrrolo[2,1-a]isoquinoline-2,3-diones and o-phenylenediamine
Surikova, O. V.
Aliev, Z. G.
Polygalova, N. N.
Mikhailovskii, A. G.
Vakhrin, M. I.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (06) : 901 - 905
[38] Synthesis of isoquinoline derivatives of quinoxalin-2-one from pyrrolo[2,1-a]isoquinoline-2,3-diones and o-phenylenediamine
O. V. Surikova
Z. G. Aliev
N. N. Polygalova
A. G. Mikhailovskii
M. I. Vakhrin
Russian Journal of Organic Chemistry, 2008, 44 : 901 - 905
[39] KF/Clinoptilolite Nanoparticles as a Heterogeneous Catalyst for Green Synthesis of pyrido[2,1-a]isoquinolines using Four-Component Reaction of Alkyl Bromides
Hamedani, Naghmeh F.
Ghazvini, Maryam
Sheikholeslami-Farahani, Fatemeh
Jamnani, Mohammad T. B.
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2019, 22 (10) : 728 - 739
[40] New Pyrrolo[2,1-a]phthalazine Derivatives by One-Pot Three-Component Synthesis
Dumitrascu, Florea
Caproiu, Miron Teodor
Georgescu, Florentina
Draghici, Bogdan
Popa, Marcel Mirel
Georgescu, Emilian
SYNLETT, 2010, (16) : 2407 - 2410

← 1 2 3 4 5 →