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 22 条

[21] Lewis Acid-Catalyzed Selective Synthesis of Diversely Substituted Indolo- and Pyrrolo[1,2-a]quinoxalines and Quinoxalinones by Modified Pictet-Spengler Reaction [J].