New N-nitrosoamines. 1. Synthesis and nitrosative cleavage of the Mannich bases derived from nitrogen-containing heterocycles and primary aliphatic amines |
| |
| Authors: | Korepin A. G. Galkin P. V. Glushakova N. M. Lodygina V. P. Eremenko I. L. Nefedov S. E. Eremenko L. T. |
| |
| Affiliation: | (1) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 18 Institutskii prosp., 142432 Chernogolovka, Moscow Region, Russian Federation;(2) N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991 Moscow, Russian Federation |
| |
| Abstract: | 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. |
| |
| Keywords: | aminomethylation nitrogen-containing heterocycles primary aliphatic amines nitrosative cleavage of tertiary amines N-nitrosoamines X-ray diffraction analysis 1H NMR and IR spectroscopy |
| 本文献已被 SpringerLink 等数据库收录！ |
|
