Recent Advances in Nitrogen-Nitrogen Bond Formation

被引:48
作者
Guo, Qihang [1 ]
Lu, Zhan [1 ]
机构
[1] Zhejiang Univ, Dept Chem, 866 Yuhangtang Rd, Hangzhou 310058, Zhejiang, Peoples R China
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 17期
关键词
nitrogen-nitrogen bond formation; heterocycles; cyclization; copper catalysis; anodic oxidation; N-N-BOND; C-N; CONSECUTIVE CONDENSATION; EFFICIENT SYNTHESIS; TRANSITION-METAL; BIOSYNTHESIS; 1H-INDAZOLES; CYCLIZATION; 1,2,3-TRIAZOLES; TOSYLHYDRAZONES;
D O I
10.1055/s-0036-1588512
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Over the last decade, N-N bond formation as a synthetic strategy has emerged as a powerful key step in the construction of highly valuable heterocycles from easily obtained materials. This review focuses on recent methods used to build N-N bonds, classified by intra- and intermolecular reactions with various types of N-X (O, C, N, H) bond cleavage. 1 Introduction 2 Intramolecular N-N Bond Formation 2.1 Cleavage of N-O Bonds 2.2 Cleavage of N-C Bonds 2.3 Cleavage of N-N Bonds 2.4 Cleavage of N-H Bonds 2.4.1 Construction of Pyrazole Derivatives 2.4.2 Construction of Triazole Derivatives 2.4.3 Construction of Indazole and Pyrazoline Derivatives 2.4.4 Construction of Other N-N Bond Derivatives 3 Intermolecular N-N Bond Formation 4 Conclusion
引用
收藏
页码:3835 / 3847
页数:13
相关论文
共 77 条
[61]   ALTERNATIVE PROCEDURES FOR PREPARING HMX [J].
SIELE, VI ;
WARMAN, M ;
LECCACORVI, J ;
HUTCHINSON, RW ;
MOTTO, R ;
GILBERT, EE ;
BENZINGER, TM ;
COBURN, MD ;
ROHWER, RK ;
DAVEY, RK .
PROPELLANTS AND EXPLOSIVES, 1981, 6 (03) :67-73
[62]   I2/KI-Mediated Oxidative N-N Bond Formation for the Synthesis of 1,5-Fused 1,2,4-Triazoles from N-Aryl Amidines [J].
Song, Lina ;
Tian, Xianhai ;
Lv, Zhigang ;
Li, Ertong ;
Wu, Jie ;
Liu, Yangxue ;
Yu, Wenquan ;
Chang, Junbiao .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14) :7219-7225
[63]   Intramolecular Fe(II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides [J].
Stokes, Benjamin J. ;
Vogel, Carl V. ;
Urnezis, Linda K. ;
Pan, Minjie ;
Driver, Tom G. .
ORGANIC LETTERS, 2010, 12 (12) :2884-2887
[64]   An efficient copper-catalyzed formation of highly substituted pyrazoles using molecular oxygen as the oxidant [J].
Suri, Mamta ;
Jousseaume, Thierry ;
Neumann, Julia J. ;
Glorius, Frank .
GREEN CHEMISTRY, 2012, 14 (08) :2193-2196
[65]   Practical synthesis of pyrazoles via a copper-catalyzed relay oxidation strategy [J].
Tang, Xiaodong ;
Huang, Liangbin ;
Yang, Jidan ;
Xu, Yanli ;
Wu, Wanqing ;
Jiang, Huanfeng .
CHEMICAL COMMUNICATIONS, 2014, 50 (94) :14793-14796
[66]   Valanimycin biosynthesis: Investigations of the mechanism of isobutylhydroxylamine incorporation [J].
Tao, T ;
Alemany, LB ;
Parry, RJ .
ORGANIC LETTERS, 2003, 5 (08) :1213-1215
[67]   Facile Synthesis of 1,2,4-Triazoles via a Copper-Catalyzed Tandem Addition-Oxidative Cyclization [J].
Ueda, Satoshi ;
Nagasawa, Hideko .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (42) :15080-+
[68]   Synthesis of 1H-Indazoles from Imidates and Nitrosobenzenes via Synergistic Rhodium/Copper Catalysis [J].
Wang, Qiang ;
Li, Xingwei .
ORGANIC LETTERS, 2016, 18 (09) :2102-2105
[69]  
Wilier RL, 1983, PROPELL EXPLOS PYROT, V8, P65, DOI [10.1002/prep.830080302, DOI 10.1002/PREP.830080302]
[70]   Synthesis of N-Arylindazoles and Benzimidazoles from a Common Intermediate [J].
Wray, Brenda C. ;
Stambuli, James P. .
ORGANIC LETTERS, 2010, 12 (20) :4576-4579