Nitropyrazoles 23. Synthesis of substituted N-amino-3-nitro-5-R-pyrazoles

被引:0
作者
A. V. Kormanov
T. K. Shkineva
I. A. Vatsadze
S. A. Shevelev
I. L. Dalinger
机构
[1] Russian Academy of Sciences,N. D. Zelinsky Institute of Organic Chemistry
来源
Russian Chemical Bulletin | 2014年 / 63卷
关键词
pyrazole; nitro group; nitropyrazoles; aminopyrazoles; aminodinitropyrazoles; nucleophilic substitution; protecting group; acylation; azomethines; energetic compounds;
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学科分类号
摘要
The study is devoted to nucleophilic substitution of nitro groups in 1-amino-3,5-dinitropyrazole (1) and its amino group derived analogs. Compound 1 upon treatment with S-nucleophiles undergoes regioselective substitution of the nitro group at position 5. Azomethine 5 obtained by the condensation of 1 with benzaldehyde gives the nucleophilic substitution reaction with S-, O-and N-nucleophiles also with involvement of the nitro group at position 5. The synthesized 5-R-substituted azomethines 7–9 upon treatment with hydrazine hydrate form N-amino-5-R-3-nitropyrazoles and benzaldazine.
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页码:435 / 442
页数:7
相关论文
共 273 条
[41]  
Cho J R(1993)undefined Adv. Heterocyclic Chem. 53 85-undefined
[42]  
Goh E M(1994)undefined Pharm. Chem. J. 21 51-undefined
[43]  
Kim J K(2001)undefined Russ. J. Org. Chem. 37 1158-undefined
[44]  
Gobel M(1980)undefined Chem. Heterocycl. Compd. 16 194-undefined
[45]  
Karaghiosoff K(1998)undefined Russ. J. Org. Chem. 34 1032-undefined
[46]  
Klapötke T M(2009)undefined Synthetic Comm. 39 4282-undefined
[47]  
Piercey D G(2009)undefined Russ. Chem. Rev. (Engl Transl.) 78 589-undefined
[48]  
Stierstorfer J(2009)undefined J. Med. Chem. 52 637-undefined
[49]  
Klapötke T M(2012)undefined Mendeleev Commun. 22 43-undefined
[50]  
Preimesser A(2012)undefined Synthesis 44 2058-undefined