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

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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. RCH2NBui 2 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. RCH2NBui 2 affords diisobutylnitrosamine, while imidazolidines transform into dinitroso compounds RCH2N(NO)CH2CH2N(NO)CH2R.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 18 Institutskii prosp., 142432, Chernogolovka, Moscow Region, Russian Federation

    A. G. Korepin, P. V. Galkin, N. M. Glushakova, V. P. Lodygina & L. T. Eremenko

  2. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    I. L. Eremenko & S. E. Nefedov

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  1. A. G. Korepin
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  2. P. V. Galkin
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  3. N. M. Glushakova
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  4. V. P. Lodygina
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  5. I. L. Eremenko
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  6. S. E. Nefedov
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  7. L. T. Eremenko
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Korepin, A.G., Galkin, P.V., Glushakova, N.M. et al. New N-nitrosoamines. 1. Synthesis and nitrosative cleavage of the Mannich bases derived from nitrogen-containing heterocycles and primary aliphatic amines. Russian Chemical Bulletin 50, 1630–1638 (2001). https://doi.org/10.1023/A:1013094720611

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