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Title: Annulative Synthesis of Thiazoles and Oxazoles from Alkenyl Sulfoxides and Nitriles via Additive Pummerer Reaction
Authors: Hori, Mitsuki
Nogi, Keisuke
Nagaki, Aiichiro
Yorimitsu, Hideki
Author's alias: 堀, 充希
野木, 馨介
永木, 愛一郎
依光, 英樹
Keywords: additive Pummerer reaction
Ritter-type reaction
heterocycles
thiazoles
oxazoles
Issue Date: Jul-2019
Publisher: Wiley-VCH Verlag
Journal title: Asian Journal of Organic Chemistry
Volume: 8
Issue: 7
Start page: 1084
End page: 1087
Abstract: Pummerer‐based annulation of alkenyl sulfoxides, mainly ketene dithioacetal monoxides (KDMs), with nitriles has been developed. By means of trifluoromethanesulfonic anhydride (Tf₂O) as an activator, additive Pummerer reaction and subsequent C−S‐bond‐forming cyclization from the nitrilium intermediates furnished the corresponding thiazoles. Moreover, the nitrilium intermediates proved to be interrupted intermolecularly by H₂O to afford oxazoles instead of thiazoles.
Rights: This is the peer reviewed version of the following article: M. Hori, K. Nogi, A. Nagaki, H. Yorimitsu, Asian J. Org. Chem. 2019, 8, 1084., which has been published in final form at https://doi.org/10.1002/ajoc.201900169. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
The full-text file will be made open to the public on 22 July 2020 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
URI: http://hdl.handle.net/2433/243226
DOI(Published Version): 10.1002/ajoc.201900169
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