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Synthesis 2017; 49(08): 1839-1848
DOI: 10.1055/s-0036-1588374
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Imidazoheterocycle-Hydrazine, -Carbamate, and Imidazocinnoline Derivatives

Jing Jiao
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
b   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: maolin@wzu.edu.cn
,
Li Xu
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
,
Wenxu Zheng
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
,
Ping Xiong
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
,
Mao-Lin Hu*
b   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: maolin@wzu.edu.cn
,
Ri-Yuan Tang*
a   Department of Applied Chemistry, College of Materials and Energy, South China Agricultural University, Guangzhou 510642, P. R. of China   Email: rytang@scau.edu.cn
b   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China   Email: maolin@wzu.edu.cn
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Publication History

Received: 15 September 2016

Accepted after revision: 21 November 2016

Publication Date:
15 December 2016 (online)

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Abstract

Iron-catalyzed amination of imidazoheterocycles with diethyl azodicarboxylate (DEAD) under mild conditions has been developed. This strategy tolerates a wide range of functional groups to afford diverse imidazoheterocycle-hydrazines in moderate to excellent yields. Significantly, imidazoheterocycle hydrazines can be converted into imidazoheterocycle carbamates and imidazocinnolines.

Key words

iron - amination - imidazoheterocycle - carbamate - cinnoline

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588374.
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