New N-nitrosoamines. 1. Synthesis and nitrosative cleavage of the Mannich bases derived from nitrogen-containing heterocycles and primary aliphatic amines

被引：0
作者：
A. G. Korepin
P. V. Galkin
N. M. Glushakova
V. P. Lodygina
I. L. Eremenko
S. E. Nefedov
L. T. Eremenko
机构：
[1] Russian Academy of Sciences,Institute of Problems of Chemical Physics
[2] Russian Academy of Sciences,N. S. Kurnakov Institute of General and Inorganic Chemistry
来源：
Russian Chemical Bulletin | 2001年 / 50卷
关键词：
aminomethylation; nitrogen-containing heterocycles; primary aliphatic amines; nitrosative cleavage of tertiary amines; -nitrosoamines; X-ray diffraction analysis; H NMR and IR spectroscopy;
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摘要：
The reactions of isatin, benzotriazole, and succinimide with formaldehyde and methylamine yield monoamines RCH2N(Me)CH2R and methylenediamines RCH2N(Me)CH2N(Me)CH2R. The use of ethylenediamine as the amino component affords N,N"-disubstituted imidazolidines, while the reactions with 3-aminopropan-1-ol give N-substituted tetrahydro-1,3-oxazines. RCH2NBui2 was obtained from succinimide, formaldehyde, and diisobutylamine. Nitrosative cleavage of the amines obtained was studied; it was shown that monoamines and methylenediamines give N-nitrosoamines RCH2N(NO)Me, which were structurally characterized by X-ray diffraction analysis. RCH2NBui2 affords diisobutylnitrosamine, while imidazolidines transform into dinitroso compounds RCH2N(NO)CH2CH2N(NO)CH2R.
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页码：1630 / 1638
页数：8
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共 36 条
[1]  
Fridman A. L.(1971)undefined Usp. Khim. 40 64-undefined
[2]  
Mukhametshin F. M.(1863)undefined Lieb. Ann. 128 153-undefined
[3]  
Novikov S. S.(1879)undefined Ber. 8 1587-undefined
[4]  
Geuther A.(1906)undefined Zh. Ros. Fiz.-Khim. O-va 38 1286-undefined
[5]  
Fischer E.(1960)undefined Zh. Obshch. Khim. 30 2754-undefined
[6]  
Solonina V. A.(1965)undefined Zh. Org. Khim. 1 1758-undefined
[7]  
Yashunskii V. G.(1971)undefined Izv. Akad. Nauk SSSR, Ser. Khim. 20 2606-undefined
[8]  
Vasil'eva V. F.(1963)undefined J. Chem. Educ. 40 181-undefined
[9]  
Pormalo M. Y.(1967)undefined J. Am. Chem. Soc. 89 1147-undefined
[10]  
Plisko E. A.(1956)undefined J. Am. Chem. Soc. 78 672-undefined
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