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Molecules 2016, 21(7), 827; doi:10.3390/molecules21070827

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
Received: 10 May 2016 / Revised: 15 June 2016 / Accepted: 21 June 2016 / Published: 25 June 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [6782 KB, uploaded 21 July 2016]   |  

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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