Cs
2
CO
3
-mediated decomposition of N-tosylhydrazones
for the synthesis of azines under mild conditions
Zai-Gang Luo
1
•
Peng Liu
2
•
Yu-Yu Fang
1
•
Xue-Mei Xu
1
•
Cheng-Tao Feng
1
•
Zhong Li
1
•
Xiao-Mei Zhang
1
•
Jie He
1
Received: 26 May 2016 / Accepted: 1 August 2016 / Published online: 10 August 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract
A facile, environmentally and efficient Cs
2
CO
3
-mediated decomposition of
N-tosylhydrazones reaction has been developed for the synthesis of functionalized azines
under mild conditions. This method offers broad substrate scope, occurs as additive-free,
without strong base conditions, utilizes readily available reactants, and forms products in
good to high yields.
Graphical Abstract
R
2
R
1
R
2
R
2
R
1
R
1
Without strong base
Broad substrate scope
Additive-free
Mild conditions
N
H
N
Ts
N
N
R
1
=H,Me,MeO,CF
3
,NO
2
,F,Cl,Br
R
2
=H,Me,Ph,Benzyl
Cs
2
CO
3
(2 equiv)
MeCN,100°C,6h
2
24 examples
up to 92% isolated yield
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
1
College of Chemical Engineering, Anhui University of Science and Technology,
Huainan 232001, China
2
Guang Zhou Institutes of Biomedicine and Health, Chinese Academy of Sciences,
Guangzhou 510530, China
123
Res Chem Intermed (2017) 43:1139–1148
DOI 10.1007/s11164-016-2688-3