Synthesis of 12-oxobenzo[c]phenanthridinones and 4-substituted 3-arylisoquinolones via Vilsmeier-Haack reaction

被引：28

作者：

Khadka, Daulat Bikram

Yang, Su Hui

Cho, Suk Hee

Zhao, Chao

Cho, Won-Jea ^{[1
]}

机构：

[1] Chonnam Natl Univ, Coll Pharm, Kwangju 500757, South Korea

来源：

TETRAHEDRON | 2012年 / 68卷 / 01期

关键词：

12-Oxobenzo[c]phenanthridinone; 4-Substituted; 3-arylisoquinolone; Vilsmeier-Haack reaction; Mitsunobu reaction; Knoevenagel condensation; PROTOBERBERINE ALKALOIDS; BIOLOGICAL EVALUATION; DNA TOPOISOMERASES; INHIBITORS; FORMYLATION; ANALOGS;

D O I：

10.1016/j.tet.2011.10.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vilsmeier-Haack reaction on 3-arylisoquinolones resulted in versatile 4-formylated 3-arylisoquinolones that were further derivatized into 12-oxobenzo[c]phenanthridinones, 4-alkoxymethyl-3-arylisoquinolones, 3aryl-4-phenoxymethylisoquinolones, 4-aminomethyl-3-arylisquinolone, and 3-isoquinolinyl-2-phenyl-acrylonitrile by different synthetic strategies. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：250 / 261

页数：12

共 50 条

[21] Formation and cleavage of the quinazolinium ring in Vilsmeier-Haack formylation of 4-dialkylamino-substituted naphthalic acid derivatives [3]
Patsenker, L.D.
Ermolenko, I.G.
Artyukhova, E.E.
Krasovitskii, B.M.
Chemistry of Heterocyclic Compounds, 2000, 36 (05) : 611 - 612
[22] THIOPHEN DERIVATIVES .16. VILSMEIER-HAACK REACTION WITH 3- AND 4-METHOXYBENZO[B]THIOPHEN
RICCI, A
BALUCANI, D
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (08): : 779 - &
[23] Microwave Assisted Vilsmeier-Haack Reaction on Substituted Cyclohex-anone Hydrazones: Synthesis of Novel 4,5,6,7-Tetrahydroindazole Derivatives
Kaur, Aneet Kamal
Bala, Renu
Kumari, Poonam
Sood, Sumit
Singh, Karan
LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (03) : 170 - 175
[24] Polyfunctional Imidazoles: I. Synthesis of 1-Substituted 4-Chloro-1H-imidazole-5-carbaldehydes by Vilsmeier-Haack Reaction
Chornous, V. A.
Bratenko, M. K.
Vovk, M. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 45 (08) : 1210 - 1213
[25] Polyfunctional imidazoles: I. Synthesis of 1-substituted 4-chloro-1H-imidazole-5-carbaldehydes by Vilsmeier-Haack reaction
V. A. Chornous
M. K. Bratenko
M. V. Vovk
Russian Journal of Organic Chemistry, 2009, 45 : 1210 - 1213
[26] Synthesis and characterization of some novel 4-formyl pyrazolylthiazoles of potential medicinal interest using Vilsmeier-Haack reaction
Sharma, PK
Singh, K
Dhawan, SN
Singh, SP
INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 2002, 41 (10): : 2071 - 2075
[27] STUDIES ON THE VILSMEIER-HAACK REACTION .13. NOVEL HETEROCYCLO-SUBSTITUTED 4,4'-BI-PYRAZOLYL DITHIOCARBAMATE DERIVATIVES
AWAD, IMA
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 1993, 56 (04) : 339 - 345
[28] STUDIES ON THE VILSMEIER-HAACK REACTION .13. NOVEL HETEROCYCLO-SUBSTITUTED 4,4'-BI-PYRAZOLYL DITHIOCARBAMATE DERIVATIVES
AWAD, IMA
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 78 (1-4): : 237 - 249
[29] Facile synthesis of 12-ketoquiuo [2,1-b]quinazolines via the Vilsmeier-Haack reaction of 6-nitro-2-methyl-3-aryl-4(3H)quinazolones
Bhatti, HS
Seshadri, S
SYNTHETIC COMMUNICATIONS, 2005, 35 (07) : 907 - 912
[30] STUDIES ON THE VILSMEIER-HAACK REACTION .3. REACTION OF 3-METHYL-1-PHENYL-4-ARYLIDENE-2-PYRAZOLIN-5-THIONE
AWAD, IMA
HASSAN, KM
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1989, 45 (3-4): : 155 - 159

← 1 2 3 4 5 →