Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions

Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions N Ts Cs CO (2 equiv) N 2 3 2 R 2 R MeCN,100°C,6h 1 R R =H, Me, MeO, CF ,NO ,F,Cl,Br 24 examples 1 3 2 up to 92% isolated yield R =H, Me, Ph, Benzyl Without strong base Additive-free Broad substrate scope Mild conditions Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2688-3) contains supplementary material, which is available to authorized users. & Zai-Gang Luo luozi139@163.com & Jie He aust_jhe@163.com College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, China Guang Zhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China 123 1140 Z.-G. Luo et al. Keywords Decomposition  N-Tosylhydrazones  Cs CO  Azines 2 3 Introduction Azines, N–N linked diimines, which exhibit interesting biological [1–3], conductive [4–6], and optical [7–9] properties and are extensively used as synthetic intermediates [10–14], have received increasing attention in recent years. Generally, azines are prepared by the condensation of aldehydes or ketones with hydrazine hydrate in solution under refluxing conditions or with promoters such as iodine or acid [15–17]. These reactions proceed rapidly but often generate large amounts of unwanted byproducts. Very recently, Peltier et al. [18] reported the first examples http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Cs2CO3-mediated decomposition of N-tosylhydrazones for the synthesis of azines under mild conditions

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Publisher
Springer Netherlands
Copyright
Copyright © 2016 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-016-2688-3
Publisher site
See Article on Publisher Site

Abstract

N Ts Cs CO (2 equiv) N 2 3 2 R 2 R MeCN,100°C,6h 1 R R =H, Me, MeO, CF ,NO ,F,Cl,Br 24 examples 1 3 2 up to 92% isolated yield R =H, Me, Ph, Benzyl Without strong base Additive-free Broad substrate scope Mild conditions Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2688-3) contains supplementary material, which is available to authorized users. & Zai-Gang Luo luozi139@163.com & Jie He aust_jhe@163.com College of Chemical Engineering, Anhui University of Science and Technology, Huainan 232001, China Guang Zhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China 123 1140 Z.-G. Luo et al. Keywords Decomposition  N-Tosylhydrazones  Cs CO  Azines 2 3 Introduction Azines, N–N linked diimines, which exhibit interesting biological [1–3], conductive [4–6], and optical [7–9] properties and are extensively used as synthetic intermediates [10–14], have received increasing attention in recent years. Generally, azines are prepared by the condensation of aldehydes or ketones with hydrazine hydrate in solution under refluxing conditions or with promoters such as iodine or acid [15–17]. These reactions proceed rapidly but often generate large amounts of unwanted byproducts. Very recently, Peltier et al. [18] reported the first examples

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Aug 10, 2016

References

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