Unusual formation of imidazooxazolone in the reaction of 1-[(2-Acetylamino)ethyl]imidazolone with KSCN in the presence of AcOH

1-[(2-Acetylamino)ethyl]imidazolone was introduced for the first time in the condensation with KSCN in the presence of AcOH and imidazooxazolone was unexpectedly obtained. This result was possible only because of the unique character of 1-((2-Acetylamino)ethyl)imidazolone, which has an intramolecular N-H...O-H hydrogen bond and, therefore, reacts with the NCS anion to give only imidazooxazolone.

Authors
Baranov V.V. 1, 2 , Antonova M.M.1 , Karnoukhova V.A.3 , Kravchenko A.N.1
Journal
Arkivoc
Number of issue
3
Language
English
Pages
63-72
Status
Published
Link
External link
DOI
10.3998/ARK.5550190.P010.048
Volume
2017
Year
2017
Organizations
  • 1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 119 991, Russian Federation
  • 2 Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation
  • 3 A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, 119991, Russian Federation
Keywords
Acoh; Fused oxazolinones; Glycoluril analogues; Imidazolinones; Kscn; X-ray diffraction
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