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Synlett 2019; 30(09): 1026-1036
DOI: 10.1055/s-0037-1611476
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© Georg Thieme Verlag Stuttgart · New York

Recent Developments in the Synthesis of Nitrogen-Containing Heterocycles through C–H/N–H Bond Functionalizations and Oxidative Cyclization

Xiang Liu  *
a   College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002, P. R. of China   Email: xiang.liu@ctgu.edu.cn
g   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, Gansu, P. R. of China   Email: chbh@lzu.edu.cn
,
Yu Huang
a   College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002, P. R. of China   Email: xiang.liu@ctgu.edu.cn
g   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, Gansu, P. R. of China   Email: chbh@lzu.edu.cn
,
Xu Meng
b   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute of LICP, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
,
Jihui Li
c   College of Materials and Chemical Engineering, Hainan University, Haikou 570228, P. R. of China
,
Dong Wang
d   Center for AIE Research, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518060, P. R. of China
,
Yongxin Chen
e   Key Laboratory of Petroleum Resources, Gansu Province and Key Laboratory of Petroleum Resources Research, Institute of Geology and Geophysics, Chinese Academy of Sciences, Lanzhou 730000, P. R. of China
,
Dong Tang
f   Ningxia Academy of Agriculture and Forestry Sciences, Yinchuan 750002, P. R. of China
,
Baohua Chen  *
g   State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, Gansu, P. R. of China   Email: chbh@lzu.edu.cn
› Author Affiliations
We gratefully acknowledge the invaluable contributions from talented students and colleagues in our laboratories, and financial support from the National Natural Science Foundation of China (Grants Nos. 21805166, 21801053, and 21403256), the 111 Project of Hubei Province (Grant No. 2018-19-1), The Youth Innovation Promotion Association CAS (2018456), China Three Gorges University, Hainan University, Shenzhen University, Lanzhou University, and the Chinese Academy of Sciences.
Further Information

Publication History

Received: 02 December 2018

Accepted after revision: 23 January 2019

Publication Date:
22 February 2019 (online)

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Dedicated to Professor Dong-Sheng Li on the occasion of his 50th birthday.

Abstract

The synthesis and structure of nitrogen-containing heterocycles are fascinating because these compounds have a great richness of structural, physicochemical, and biological properties. Therefore, the development of improved ways for the synthesis of polyfunctional nitrogen-containing heterocycles continues to be a challenging goal. This account describes developments in the discovery of C–H/N–H bond functionalization and oxidative cyclization procedures for the synthesis of nitrogen-containing heterocycles (aziridines, indoles, indolizines, triazoles, imidazoles, oxazoles, thiazoles, quinoxalines, triazines, and pyridines) in our laboratories during the last 15 years.

1 Introduction

2 Synthesis of Aziridines

3 Synthesis of Indoles and Indolizines

4 Synthesis of Triazoles

5 Synthesis of Imidazoles

6 Synthesis of Oxazoles and Thiazoles

7 Synthesis of Quinoxalines, Triazines, and Pyridines

8 Conclusion and Outlook

Key words

oxidative cyclization - C–H bond activation - nitrogen heterocycles - N–H bond activation