InCl3-Driven Regioselective Synthesis of Functionalized/Annulated Quinolines: Scope and Limitations

被引：72

作者：

Chanda, Tanmoy ^{[1
]}

Verma, Rajiv Kumar ^{[1
]}

Singh, Maya Shankar ^{[1
]}

机构：

[1] Banaras Hindu Univ, Dept Chem, Fac Sci, Varanasi 221005, Uttar Pradesh, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2012年 / 7卷 / 04期

关键词：

annulation; cyclization; indium; quinolines; solvent-free synthesis; ONE-POT SYNTHESIS; FORMAL TOTAL-SYNTHESIS; SOLVENT-FREE SYNTHESIS; ONE-STEP SYNTHESIS; CONVENIENT SYNTHESIS; SUBSTITUTED QUINOLINES; FRIEDLANDER SYNTHESIS; PHOTOPHYSICAL PROPERTIES; 2-AMINOBENZYL ALCOHOL; EFFICIENT SYNTHESIS;

D O I：

10.1002/asia.201100872

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The efficient, regioselective synthesis of functionalized/annulated quinolines was achieved by the coupling of 2-aminoaryl ketones with alkynes/active methylenes/a-oxoketene dithioacetals promoted by InCl3 in refluxing acetonitrile as well as under solvent-free conditions in excellent yields. This transformation presumably proceeded through the hydroaminationhydroarylation of alkynes, and the Friedlander annulation of active methylene compounds and a-oxoketene dithioacetals with 2-aminoarylketones. In addition, simple reductive and oxidative cyclization of 2-nitrobenzaldehyde and 2-aminobenzylalcohol, respectively, afforded substituted quinolines. Systematic optimization of the reaction parameters allowed us to identify two-component coupling (2CC) conditions that were tolerant of a wide range of functional groups, thereby providing densely functionalized/annulated quinolines. This approach tolerates the synthesis of various bioactive quinoline frameworks from the same 2-aminoarylketones under mild conditions, thus making this strategy highly useful in diversity-oriented synthesis (DOS). The scope and limitations of the alkyne-, activated methylene-, and a-oxoketene dithioacetal components on the reaction were also investigated.

引用

页码：778 / 787

页数：10

共 200 条

[11] A simple, efficient and solvent-free protocol for the Friedlander synthesis of quinolines by using SnCl2 • 2H2O [J].