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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 3
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Original Articles

Synthesis of Quinolines by N-Deformylation and Aromatization via Solvent-Free, High-Speed Ball Milling

, &
Pages 361-374 | Received 25 Feb 2011, Published online: 02 Nov 2012
 

Abstract

The emerging technique of high-speed ball milling was first applied in the N-deformylation and aromatization reaction to synthesize quinolines. PEGs (polyglycols) were used to promote this solvent-free, solid-solid state reaction and good to excellent yields of the quinolines were obtained in short reaction times.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We are grateful to the National Natural Science Foundation of China (No. 20876147) and Natural Science Foundation of Zhejiang Province (No. Y4090346) for financial support.

Notes

a Reactions were run with 5 mmol of 1a, 10 mol% of PEGs, and 5.0 g NaCl.

b Isolated yields.

c 32 wt% KF.

a Reactions were carried out with N-formyl-1,2-dihydroquinolines 1 (5 mmol), NaOH (0.3 g, 7.5 mmol), PEG 2000 (1 g, 0.5 mmol), and NaCl (5.0 g).

b Isolated yields based on 1.

c NaOH (0.4 g, 10 mmol) was used.

a 5 mmol of 1a, 10 mol% of PEG, and 5.0 g NaCl were used.

b The recovered reagent (including NaOH) was used with the addition of fresh 1.0 equiv. NaOH.

c Isolated yields.

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