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Chem Asian J. 2012 Apr;7(4):778-87. doi: 10.1002/asia.201100872. Epub 2012 Feb 6.

InCl3-driven regioselective synthesis of functionalized/annulated quinolines: scope and limitations.

Author information

1
Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221005, India.

Abstract

The efficient, regioselective synthesis of functionalized/annulated quinolines was achieved by the coupling of 2-aminoaryl ketones with alkynes/active methylenes/α-oxoketene dithioacetals promoted by InCl(3) in refluxing acetonitrile as well as under solvent-free conditions in excellent yields. This transformation presumably proceeded through the hydroamination-hydroarylation of alkynes, and the Friedländer annulation of active methylene compounds and α-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 α-oxoketene dithioacetal components on the reaction were also investigated.

PMID:
22311639
DOI:
10.1002/asia.201100872
[Indexed for MEDLINE]

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