Unusual Friedlander Reactions: A Route to Novel Quinoxaline-Based Heterocycles

被引：12

作者：

Shoker, Tharallah A. ^{[2
]}

Ghattass, Khaled I. ^{[2
]}

Fettinger, James C. ^{[1
]}

Kurth, Mark J. ^{[1
]}

Haddadin, Makhluf J. ^{[2
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

[2] Amer Univ Beirut, Dept Chem, Beirut, Lebanon

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 14期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

COMPLEXES;

D O I：

10.1021/ol301550e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid catalyzed Friedlander reactions of a number of 2,3-dihydro-1H-cyclopenta[b]quinoxaline-1-ones with 2-aminobenzaldehyde yield, unexpectedly, 8H-indolo[3,2-a]phenazine and quinolino[2,3-c]cyclopentadienone[2,3-b]quinoxalines, the structures of derivatives of which were confirmed by X-ray crystallography. Easy routes to novel quinoxaline-based indoles, quinolones, and quinoxaline-1,4-dioxides are reported, and proposed mechanisms for the unexpected products are discussed.

引用

页码：3704 / 3707

页数：4

共 50 条

[41] Synthesis of a fluorene and quinoxaline-based co-polymer for organic electronics
Sigl, Marco
Rath, Thomas
Schlemmer, Bettina
Fuerk, Peter
Trimmel, Gregor
MONATSHEFTE FUR CHEMIE, 2023, 154 (05): : 543 - 551
[42] Quinoxaline-based inhibitors of Ebola and Marburg VP40 egress
Loughran, H. Marie
Han, Ziying
Wrobel, Jay E.
Decker, Sarah E.
Ruthel, Gordon
Freedman, Bruce D.
Harty, Ronald N.
Reitz, Allen B.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (15) : 3429 - 3435
[43] The Benzyl Moiety in a Quinoxaline-Based Scaffold Acts as a DNA Intercalation Switch
Mahata, Tridib
Kanungo, Ajay
Ganguly, Sudakshina
Modugula, Eswar Kalyan
Choudhury, Susobhan
Pal, Samir Kumar
Basu, Gautam
Dutta, Sanjay
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) : 7733 - 7736
[44] Quinoxaline-based host materials for organic light-emitting diodes
Chuang, Ting-Hsuan
Su, Kuan-Yu
Yang, Yu-Ru
Chen, Yi-Ting
Hsu, Ching-Yung
He, Zih-Ru
Lu, Chin-Wei
Chang, Chih-Hao
OPTICAL MATERIALS, 2025, 159
[45] Synthesis of a fluorene and quinoxaline-based co-polymer for organic electronics
Marco Sigl
Thomas Rath
Bettina Schlemmer
Peter Fürk
Gregor Trimmel
Monatshefte für Chemie - Chemical Monthly, 2023, 154 : 543 - 551
[46] Synthesis and Photovoltaic Properties of Quinoxaline-Based Semiconducting Polymers with Fluoro Atoms
Song, Suhee
Choi, Hyo Il
Shin, In Soo
Suh, Hongsuk
Hyun, Myung Ho
Lee, Gun Dae
Park, Seong Soo
Park, Sung Heum
Jin, Youngeup
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (08) : 2245 - 2250
[47] Impact of π-conjugation configurations on the photovoltaic performance of the quinoxaline-based organic dyes
Ma, Liang-Wei
Huang, Zu-Sheng
Wang, Sheng
Meier, Herbert
Cao, Derong
DYES AND PIGMENTS, 2017, 145 : 126 - 135
[48] Quinoxaline-based Y-type acceptors for organic solar cells
Xie, Meiling
Wei, Zhixiang
Lu, Kun
CHEMICAL SCIENCE, 2024, 15 (22) : 8265 - 8279
[49] The effect of molecular structure on the properties of quinoxaline-based molecules for OLED applications
Ledwon, Przemyslaw
Motyka, Radoslaw
Ivaniuk, Khrystyna
Pidluzhna, Anna
Martyniuk, Natalia
Stakhira, Pavlo
Baryshnikov, Glib
Minaev, Boris F.
Agren, Hans
DYES AND PIGMENTS, 2020, 173
[50] Quinoxaline-Based Scaffolds Targeting Tyrosine Kinases and Their Potential Anticancer Activity
El Newahie, Aliya M. S.
Ismail, Nasser S. M.
Abou El Ella, Dalal A.
Abouzid, Khaled A. M.
ARCHIV DER PHARMAZIE, 2016, 349 (05) : 309 - 326

← 1 2 3 4 5 →