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Synthesis 2011(20): 3267-3270  
DOI: 10.1055/s-0030-1260191
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Organic Reactions in Water: A Distinct Approach for the Synthesis of Quinoline Derivatives Starting Directly from Nitroarenes [¹]

Biswanath Das*, Paramesh Jangili, Jajula Kashanna, Rathod Aravind Kumar
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27193198; e-Mail: biswanathdas@yahoo.com;
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Publication History

Received 11 June 2011
Publication Date:
24 August 2011 (online)

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Abstract

Three-component reactions of nitroarenes, aldehydes, and phenylacetylene in the presence of indium in dilute hydrochloric acid produce the corresponding quinoline derivatives under reflux. The conversion in this one-pot synthesis involves the following steps: (i) reduction of the nitroarenes to anilines, (ii) coupling of the anilines, aldehydes, and phenylacetylene, (iii) cyclization of the resulting species, and (iv) dehydrogenation of the cyclic intermediates. Several new quinolines have been prepared.

Key words

quinolines - multicomponent reactions - one-pot synthesis - nitroarenes - indium - hydrochloric acid

1

Part 226 in the series ‘Studies on novel synthetic methodologies’.

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1

Part 226 in the series ‘Studies on novel synthetic methodologies’.