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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 7, pp 1053–1056 | Cite as

Unexpected Formation of a Tricycle in the Reaction of 1,3-Bis(Hydroxymethyl)Urea with Propane-1,3-Diamine*

  • Fares Hamoud
  • S. M. Ramsh
  • L. M. Pevzner
  • V. S. Fundamensky
  • V. V. Gurzhiy
  • V. I. Zakharov
  • V. A. Kuznetsov
  • D. V. Krivorotov
  • E. S. Khrabrova
LETTERS TO THE EDITOR

By contrast with the aminomethylation of thiourea by formaldehyde and primary amines to form 5-substituted 1,3,5-triazinane-2-thiones (see studies [1, 2] and references therein) the aminomethylation of urea has not attracted so much work [3, 4, 5, 6, 7, 8, 9, 10], the most recent being published in 1991. Because of the possibility of different condensations involving urea and formaldehyde [11, 12] cyclic urea Mannich bases are better obtained not by a three-component condensation of urea, formaldehyde, and the corresponding primary amine [3, 4, 5, 7] but rather using 1,3-dimethylolurea (DMU) (1) [13], prepared from urea and formaldehyde, which then condenses with a suitable primary amine [7, 8] or by condensing urea with the previously prepared dimethylol derivative of a primary amine with or without isolation of the indicated intermediate product [9]. The N-methylene derivative of a primary amine [10] may be used in place of the latter. Ethylenediamine and ethanolamine have been used...

Keywords

1,3-bis(hydroxymethyl)urea 1,3,5,7,11,13,15,17-octaazatricyclo[15.3.1.17,11]docosane-4 14-dione propane-1,3-diamine urea aminomethylation 

Supplementary material

10593_2014_1562_MOESM1_ESM.pdf (1.9 mb)
ESM 1 (PDF 1898 kb)
10593_2014_1562_MOESM2_ESM.pdf (967 kb)
ESM 2 (PDF 966 kb)

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Fares Hamoud
    • 1
  • S. M. Ramsh
    • 1
  • L. M. Pevzner
    • 1
  • V. S. Fundamensky
    • 1
  • V. V. Gurzhiy
    • 2
  • V. I. Zakharov
    • 3
  • V. A. Kuznetsov
    • 3
  • D. V. Krivorotov
    • 3
  • E. S. Khrabrova
    • 1
  1. 1.Saint Petersburg State Institute of Technology (Technical University)Saint PetersburgRussia
  2. 2.Saint Petersburg State UniversitySaint PetersburgRussia
  3. 3.Research Institute of Hygiene, Occupational Pathology, and Human Ecology of the Federal Medical and Biological AgencySaint PetersburgRussia

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