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Article

Ionic Liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines

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Sanjay S. Palimkar, Shapi A. Siddiqui, Thomas Daniel, Rajgopal. J. Lahoti, and Kumar V. Srinivasan*

Division of Organic Chemistry, Technology, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411 008, India

J. Org. Chem., 2003, 68 (24), pp 9371–9378

DOI: 10.1021/jo035153u

Publication Date (Web): October 24, 2003

To whom correspondence should be addressed. Tel: +91-20-588 9089. Fax: +91-20-589 3614.

, kvsri@dalton.ncl.res.in

Abstract

Several room-temperature ionic liquids (ILs) based on 1-butylimidazolium salts with varying anions were synthesized and evaluated for the preparation of biologically active substituted quinolines and fused polycyclic quinolines using the Friedlander heteroannulation reaction. On screening, 1-butylimidazolium tetrafluoroborate [Hbim]BF₄ was found to be the best ionic liquid for the heteroannulation reaction, and the reasons to this effect are well explained. The reactions proceed very well under relatively mild conditions without any added catalyst. The IL acts as a promoter for this regiospecific synthesis and can be recycled. By this green approach, various quinolines were prepared in excellent yields and purity and well-characterized.

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Published In Issue November 28, 2003
Received August 6, 2003

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Article

Ionic Liquid-Promoted Regiospecific Friedlander Annulation: Novel Synthesis of Quinolines and Fused Polycyclic Quinolines

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

A Mild and Efficient One-Step Synthesis of Quinolines

Highly Regioselective Friedländer Annulations with Unmodified Ketones Employing Novel Amine Catalysts: Syntheses of 2-Substituted Quinolines, 1,8-Naphthyridines, and Related Heterocycles

A Novel Traceless Solid-Phase Friedländer Synthesis

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