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Open AccessArticle

Dual Behavior of Iodine Species in Condensation of Anilines and Vinyl Ethers Affording 2-Methylquinolines

1
Faculty of Applied Sciences, Ton Duc Thang University, 19 Nguyen Huu Tho Street, Tan Phong Ward, District 7, Ho Chi Minh City 700000, Vietnam
2
School of Environmental Science and Technology, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan
3
Research Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan
*
Authors to whom correspondence should be addressed.
Academic Editor: Wim Dehaen
Molecules 2016, 21(7), 827; https://doi.org/10.3390/molecules21070827
Received: 10 May 2016 / Revised: 15 June 2016 / Accepted: 21 June 2016 / Published: 25 June 2016
(This article belongs to the Collection Heterocyclic Compounds)
A metal-free, mild and efficient method for the synthesis of 2-methylquinolines was successfully developed by condensation of anilines with vinyl ethers in the presence of catalytic amount of iodine. Modification of both pyridine and benzene moieties was easily achieved by changing only the vinyl ether and aniline. In this reaction, the iodine species was revealed to show dual behavior; molecular iodine serves as an oxidant, while its reduced form, hydrogen iodide, activates the vinyl ether. The redox reaction between these iodine species enables the use of a catalytic amount of iodine in this synthetic method. View Full-Text
Keywords: 2-methylquinoline; iodine-mediated reaction; aniline; vinyl ether; redox reaction 2-methylquinoline; iodine-mediated reaction; aniline; vinyl ether; redox reaction
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MDPI and ACS Style

Le, S.T.; Yasuoka, C.; Asahara, H.; Nishiwaki, N. Dual Behavior of Iodine Species in Condensation of Anilines and Vinyl Ethers Affording 2-Methylquinolines. Molecules 2016, 21, 827.

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