Hydride transfer reactions of 5-(2-alkohybenzylidene) barbituric acids: Synthesis of 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes

The thermal cyclization of 5-(2-phenoxymethylphenyl-methylene)barbituric acid and its derivatives affords 2,4,6-trioxoperhydropyrimidine-5-spiro-3′-chromanes. The reactions require no catalysts and proceed at temperatures from 118 to 240 °C depending on the substrate activity. These cyclization reactions are analogous to T-reactions of tertiary amines involving the hydride transfer. © 2016 Elsevier Ltd

Authors
Krasnov K.A. 1 , Dorovatovskii P.V. 2 , Zubavichus Y.V. 2 , Timofeeva T.V. 3 , Khrustalev V.N. 4, 5
Journal
Tetrahedron
Issue number
5
Language
English
Pages
542-549
State
Published
Link
External link
DOI
10.1016/J.TET.2016.12.045
Volume
73
Year
2017
Organizations
  • 1 Institute of Toxicology, St. Petersburg, Russian Federation
  • 2 National Research Center “Kurchatov Institute”, Moscow, Russian Federation
  • 3 New Mexico Highlands University, Las Vegas, NM, United States
  • 4 Peoples’ Friendship University of Russia (RUDN), Moscow, Russian Federation
  • 5 Nesmeyanov Institute of Organoelement Compounds of RAS, Moscow, Russian Federation
Keywords
1,5-Hydride shift; 5-(2-Alkoxyphenylmethylene)-barbituric acids; T-reaction; Thermal isomerization; Trioxoperhydropyrimidine-5-spiro-3′-chromane
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